Glycerol → 4-(Acetyloxy)-2-butanone

HRID 1165489

Reaction equation

HRID 1165489 reaction equation
[OH:1][CH2:2][CH:3](CO)O.[OH:7][CH2:8][CH2:9][C:10](=[O:12])[CH3:11].C(OCC)(=O)CC(C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[C:2]([O:7][CH2:8][CH2:9][C:10](=[O:12])[CH3:11])(=[O:1])[CH3:3]

Participants

6

Reactant 4

HCID 753GlycerolHCID 8868Ethyl AcetoacetateHCID 1115094-Hydroxy-2-ButanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 1391004-(Acetyloxy)-2-butanoneYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The method described in Example 5 is followed starting with glycerol and 4-hydroxy-2-butanone, suitably protected at the hydroxy group with an acetyl radical. 4-acetoxy-2-butanone is prepared starting from ethyl acetoacetate, protected at the carbonyl group as diethylacetal, by reduction with lithium-aluminium hydride, followed by restoring the keto group by means of silica in the presence of water (A: Banerje 8 G. P. Kalena, Synth. Commun (1982) 12, 225). 1,3-dioxolane-2-methyl-2'-(2-hydroxyethyl-4-acetylthiomethylene distills at 164°-170° C. (10 mm Hg). Yield 61%.

Workup

  1. distillation1,3-dioxolane-2-methyl-2'-(2-hydroxyethyl-4-acetylthiomethylene distills at 164°-170° C. (10 mm Hg)

Sources & evidence

ORD record
ord-2e7d0c3e6c13486b814b78a283fe37cb
Source dataset
uspto-grants-1990_03
Patent number
US04910220

Linked notes

Loading…