6975-85-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 17, p. 962, 1952 DOI: 10.1021/jo50007a009

InChI:InChI=1/C5H10O2/c1-5(6)3-4-7-2/h3-4H2,1-2H3

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 67935-23-3 3-methoxy-2-butenol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 4454-05-1 2-methoxy-3,4-dihydro-2H-pyran 
• 78-94-4 methyl vinyl ketone 
• 292638-85-8 acrylic acid methyl ester 
• 628-28-4 butyl methyl ether 
• 807364-49-4 1-(4'-nitrophenyl)-1-hydroxy-5-methoxy-3-pentanone 
• 67-56-1 methanol 

Downstream Products

• 32778-35-1 2-dimethylaminomethyl-1-buten-3-one 
• 98486-94-3 3-dimethylaminomethyl-4-methoxy-butan-2-one 
• 2543-57-9 1-Dimethylamino-3-butanon 
• 99419-33-7 4-Formyloxy-2-butanone 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 78-94-4 methyl vinyl ketone 
• 10150-87-5 1-acetoxybutan-3-one 
• 6607-66-5 1,3,3-trimethoxybutane 
• 128-38-1 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl 
• 91374-55-9 4-(3,5-di-tert-butyl-4-hydroxybenzyl)-3-methyl-2-cyclohexene-1-one 
• 91374-54-8 6-(3,5-di-tert-butyl-4-hydroxybenzyl)-3-methyl-2-cyclohexen-1-one 
• 5082-72-4 1-[3,5-di-tert-butyl-4-hydroxyphenyl]-butan-3-one 
• 67-56-1 methanol 
• 32450-56-9 retinyl methyl ether 

Relevant academic research and scientific papers

Pd(II)-catalyzed acetalization of terminal olefins with electron-withdrawing groups in supercritical carbon dioxide: selective control and mechanism

Pd(II)-catalyzed acetalization of terminal olefins with electron-withdrawing groups was carried out smoothly in supercritical carbon dioxide under oxygen atmosphere when polystyrene-supported benzoquinone (PS-BQ) or CuII (CuI) chloride was employed as cocatalyst. The higher selectivity was achieved, without any chlorinated by-product detected, when using PS-BQ instead of CuII (or CuI) chloride. PS-BQ could be recycled with excellent catalytic activity remaining after each simple filtration. Chlorine ion was demonstrated to be a promoter. The different acetalization mechanisms were revealed by the subtle relationship of chlorine ion and benzoquinone (BQ) to the catalytic activity of PdCl2/PS-BQ, PdII-CuCl2 or Pd(OAc)2/PS-BQ.

Unusual reversal of regioselectivity in antibody-mediated aldol additions with unsymmetrical methyl ketones

A catalytic regio- and enantioselective aldol reaction of various unsymmetrical methyl ketones with para-nitrobenzaldehyde has been developed using aldolase antibodies as the catalysts. It has been found that the sense and level of regioselectivity for the reactions catalysed by antibody 38C2 and 33F12 are highly dependent on the structure of both the donor and the acceptor but in contrast, antibodies 84G3 and 93F3 catalyse the exclusive formation of the linear regioisomer independent of the structure of the reactants examined. The level of enantiocontrol is very high for most reactions. Both linear aldol enantiomers could be accessed through aldol or retro-aldol reactions using the same antibody. Theoretical studies on regioisomeric α- and β-heteroatom substituted enamines derived from unsymmetrical ketones suggest that most of the linear aldol products formed in the presence of antibodies 84G3 and 93F3 must be formed from intermediate enamines which are not the thermodynamically most favourable.

Products of the gas-phase reactions of the OH radical with n-butyl methyl ether and 2-isopropoxyethanol: Reactions of ROC(O)

The products of the gas-phase reactions of the OH radical with n-butyl methyl ether and 2-isopropoxyethanol in the presence of NO have been investigated at 298±2 K and 740 Torr total pressure of air by gas chromatography and in situ atmospheric pressure ionization tandem mass spectrometry. The products observed from n-butyl methyl ether were methyl formate, propanal, butanal, methyl butyrate, and CH3C(O)CH2CH2OCH3 and/or CH3CH2C(O)CH2OCH3, with molar formation yields of 0.51±0.11, 0.43±0.06, 0.045±0.010, approximately 0.016, and 0.19±0.04, respectively. Additional products of molecular weight 118, 149 and 165 were observed by API-MS/MS analyses, with those of molecular weight 149 and 165 being identified as organic nitrates. The products observed and quantified from 2-isopropoxyethanol were isopropyl formate and 2-hydroxyethyl acetate, with molar formation yields of 0.57±0.05 and 0.44±0.05, respectively. For both compounds, the majority of the reaction products and reaction pathways are accounted for, and detailed reaction mechanisms are presented. The results of this product study are combined with previous literature product data to investigate the tropospheric reactions of R1R2C(O)OR radicals formed from ethers and glycol ethers, leading to a revised estimation method for the calculation of reaction rates of alkoxy radicals.

REACTION DES VINYLOGUES D'HEMIACETALS ET DE LEURS EQUIVALENTS SYNTHETIQUES SUR LES ETHERS D'ENOLS HETEROCYCLIQUES

We describe the reaction of hemiacetal vinylogs 2 or their synthetic equivalent with cyclic enol ethers 1 yielding ketoacetals 3.Acidic treatment of these compounds leads to bicyclic heterocycles 8 or enone aldehyde 12 depending on the nature of substituents R1.

Phase-Transfer Catalyzed Reactions. 5. Dramatic Effect of the Concentration of Base on the Dimerization of Crotonaldehyde

Self-condensation of crotonaldehyde under base-catalyzed phase-transfer conditions leads to aldehydes 3 or 4, depending only on the concentration of aqueous hydroxide used.Quaternary ammonium fluorides in anhydrous THF is shown to be a useful system for conjugate additions involving base-sensitive aldehydes.