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Carboxylic acid synthesis by oxidation of alcohols

Synthesis of Alcohols

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Synthesis of homopropargyl alcohols via sonochemical Barbier ..

Synthesis and Reactions of Ethers
In the Williamson ether synthesis, alkoxide ions react with zero degree or primary alkyl halides to form ethers. Ethers are cleaved with hydrogen halides to form alkyl halides and alcohols. The alkyl group in the alkyl halide is the least hindered alkyl group in the ether.

Stereodivergent Synthesis of the Diamino Alcohol Core of Ritonavir and Its C-2 Epimer

AB - The prevalence of amide functionality in organic chemistry has prompted the development of numerous protocols for amide synthesis. Nevertheless, amidation procedures reported to date require stoichiometric amounts of reagents and consequently generate equimolar amounts of by-products. In contrast, the direct amidation of amines with alcohol with concomitant liberation of 2 equiv of dihydrogen is an environmentally benign strategy to prepare molecular entities containing amide bonds (Scheme 1). During the course of this research, a new catalytic system that successfully promotes the direct synthesis of amides from alcohols and amines was discovered. (Chemical Equation Presented) The initial experiment involved 2-phenylethanol, benzylamine, and 5% catalyst generated in situ from Ru(PPh3)3Cl2, imidazolium salt A, and potassium tert-butoxide (Fig. 1). The reaction produced N-benzyl 2-phenylacetamide in 15% yield as well as a substantial amount of unreacted alcohol and amine (Table 1, entry 1). Upon replacement of ruthenium precatalyst with Ru(COD)Cl2 and without the phosphine ligand, amidation failed to occur (entry 2). However, the use of monodentate ligands having a larger cone angle slightly improved the yield of the amide (entries 3-6). (Table Presented) Alternatively, variation of carbene precursors has a remarkable influence on the amidation (entries 8-14), with precursor D providing the best result. Subsequently, precursor D was used to explore variation of phosphine ligands (entries 15-19). Although PCyp3 gave the best yield (entry 18), the more stable and crystalline HBF4 salt (entry 19) was used to examine the scope and limitation of the method. A variety of primary alcohols reacted with primary amines under optimized conditions to produce the corresponding secondary amides in very satisfactory yields (Table 2, entries 1-9). Noticeably, the unhindered alcohols and amines delivered the amide in excellent yield (entries 1 and 2). However, aniline and secondary amines were unreactive at 110°C, although raising the temperature to 163°C afforded amide, albeit in moderate yield (entries 10 and 11). Presumably, the amidation sequence does not involve an intermediate ester but proceeds through an aldehyde that is coordinated to the metal (Scheme 2). The hemiaminal generated upon introduction of amine also remained attached to the metal. The subsequent β-hydride elimination completes the catalytic cycle and delivers the amide without concomitant release of aldehyde or hemiaminal. (Chemical Equation Presented)

A series of homopropargyl alcohols were synthesized from ..

Synthesis of homopropargyl alcohols …

The prevalence of amide functionality in organic chemistry has prompted the development of numerous protocols for amide synthesis. Nevertheless, amidation procedures reported to date require stoichiometric amounts of reagents and consequently generate equimolar amounts of by-products. In contrast, the direct amidation of amines with alcohol with concomitant liberation of 2 equiv of dihydrogen is an environmentally benign strategy to prepare molecular entities containing amide bonds (Scheme 1). During the course of this research, a new catalytic system that successfully promotes the direct synthesis of amides from alcohols and amines was discovered. (Chemical Equation Presented) The initial experiment involved 2-phenylethanol, benzylamine, and 5% catalyst generated in situ from Ru(PPh3)3Cl2, imidazolium salt A, and potassium tert-butoxide (Fig. 1). The reaction produced N-benzyl 2-phenylacetamide in 15% yield as well as a substantial amount of unreacted alcohol and amine (Table 1, entry 1). Upon replacement of ruthenium precatalyst with Ru(COD)Cl2 and without the phosphine ligand, amidation failed to occur (entry 2). However, the use of monodentate ligands having a larger cone angle slightly improved the yield of the amide (entries 3-6). (Table Presented) Alternatively, variation of carbene precursors has a remarkable influence on the amidation (entries 8-14), with precursor D providing the best result. Subsequently, precursor D was used to explore variation of phosphine ligands (entries 15-19). Although PCyp3 gave the best yield (entry 18), the more stable and crystalline HBF4 salt (entry 19) was used to examine the scope and limitation of the method. A variety of primary alcohols reacted with primary amines under optimized conditions to produce the corresponding secondary amides in very satisfactory yields (Table 2, entries 1-9). Noticeably, the unhindered alcohols and amines delivered the amide in excellent yield (entries 1 and 2). However, aniline and secondary amines were unreactive at 110°C, although raising the temperature to 163°C afforded amide, albeit in moderate yield (entries 10 and 11). Presumably, the amidation sequence does not involve an intermediate ester but proceeds through an aldehyde that is coordinated to the metal (Scheme 2). The hemiaminal generated upon introduction of amine also remained attached to the metal. The subsequent β-hydride elimination completes the catalytic cycle and delivers the amide without concomitant release of aldehyde or hemiaminal. (Chemical Equation Presented)

Synthesis of Alcohols
Alkenes react with water, in the presence of acid, to yield alcohols. The mechanism follows Markovnikov addition. Alkyl halides react with hydroxide to produce alcohols. Organolithium or Grignard reagents add to aldehydes and ketones to produce alcohols. Hydrogen, from sodium borohydride, lithium aluminum hydride, or hydrogen, adds to aldehydes and ketones to produce alcohols.

Dehydration of Alcohols Mechanism | Dehydration of synthesis

Chapter 10: Structure and Synthesis of Alcohols …

N2 - The prevalence of amide functionality in organic chemistry has prompted the development of numerous protocols for amide synthesis. Nevertheless, amidation procedures reported to date require stoichiometric amounts of reagents and consequently generate equimolar amounts of by-products. In contrast, the direct amidation of amines with alcohol with concomitant liberation of 2 equiv of dihydrogen is an environmentally benign strategy to prepare molecular entities containing amide bonds (Scheme 1). During the course of this research, a new catalytic system that successfully promotes the direct synthesis of amides from alcohols and amines was discovered. (Chemical Equation Presented) The initial experiment involved 2-phenylethanol, benzylamine, and 5% catalyst generated in situ from Ru(PPh3)3Cl2, imidazolium salt A, and potassium tert-butoxide (Fig. 1). The reaction produced N-benzyl 2-phenylacetamide in 15% yield as well as a substantial amount of unreacted alcohol and amine (Table 1, entry 1). Upon replacement of ruthenium precatalyst with Ru(COD)Cl2 and without the phosphine ligand, amidation failed to occur (entry 2). However, the use of monodentate ligands having a larger cone angle slightly improved the yield of the amide (entries 3-6). (Table Presented) Alternatively, variation of carbene precursors has a remarkable influence on the amidation (entries 8-14), with precursor D providing the best result. Subsequently, precursor D was used to explore variation of phosphine ligands (entries 15-19). Although PCyp3 gave the best yield (entry 18), the more stable and crystalline HBF4 salt (entry 19) was used to examine the scope and limitation of the method. A variety of primary alcohols reacted with primary amines under optimized conditions to produce the corresponding secondary amides in very satisfactory yields (Table 2, entries 1-9). Noticeably, the unhindered alcohols and amines delivered the amide in excellent yield (entries 1 and 2). However, aniline and secondary amines were unreactive at 110°C, although raising the temperature to 163°C afforded amide, albeit in moderate yield (entries 10 and 11). Presumably, the amidation sequence does not involve an intermediate ester but proceeds through an aldehyde that is coordinated to the metal (Scheme 2). The hemiaminal generated upon introduction of amine also remained attached to the metal. The subsequent β-hydride elimination completes the catalytic cycle and delivers the amide without concomitant release of aldehyde or hemiaminal. (Chemical Equation Presented)

Alcohols are a family of organic (carbon-based) compounds. Ethanol is an alcohol that can be produced by fermentation or by direct synthesis from crude oil products.

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Amide synthesis from alcohols and amines by the …

The competitive landscape between synthetic and natural alcohols has changed with oil prices. First, rising oil prices made synthetic alcohols less competitive than in the past, but more recently—in 2016—low oil prices, and high palm and palm kernel prices made synthetic alcohols competitive again. The advantage of natural producers over synthetic producers led to significant capacity increases in the natural alcohols sector. But the new capacity installed in Asia over the last several years has led to a severe overcapacity situation. Price volatility in this market will likely continue into the foreseeable future, driven by price fluctuations in feedstock (both oleochemicals and crude oil).

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