2-[(Acetyloxy)methyl]-4-(benzyloxy)butyl acetate → 1,4-Butanediol, 2-[(acetyloxy)methyl]-, 1-acetate

HRID 1368677Notes

Reaction equation

HRID 1368677 reaction equation
[C:1]([O:4][CH2:5][CH:6]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:7][CH2:8][O:9]CC1C=CC=CC=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:4][CH2:5][CH:6]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:7][CH2:8][OH:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 97961422-[(Acetyloxy)methyl]-4-(benzyloxy)butyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 101766101,4-Butanediol, 2-[(acetyloxy)methyl]-, 1-acetateYield 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-acetoxymethyl-4-benzyloxy-but-1-yl acetate (55 g, 0.187 mol) in ethanol (250 ml) was added 10% palladium on carbon (2.5 g), and the mixture hydrogenated at atmospheric pressure and room temperature. When the theoretical hydrogen uptake had been achieved (18 hours), the reaction was stopped and filtered through Celite. Evaporation of the filtrate gave a colourless oil (35 g). This was purified by column chromatography on silica gel, elution with 2% methanol in chloroform affording 2-acetoxy-methyl-4-hydroxybut-1-yl acetate as a clear oil (32.9, 86%). δH (CDCl3) 1.61 (2H, q, CHCH2CH2), 2.04 (6H, s, 2×OCOCH3), 2.20 (1H, m, CH), 2.61 (1H, br s, D2O exchangeable, OH), 3.68 (2H, t, CH2OH), 4.04 (4H, d, 2×CH2OCOCH3).

Workup

  1. customhydrogenated at atmospheric pressure and room temperature
  2. custom(18 hours)
  3. filtrationfiltered through Celite
  4. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-91c3b220d3804dbe9ea60c11f42b9dc3
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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