Dimethyl malate → 3,4-Dihydroxybutanoic acid gamma-lactone

HRID 907581

Reaction equation

HRID 907581 reaction equation
[C:1](OC)(=[O:9])[CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[OH:3].C(O)C(O)CCO>CO>[OH:3][CH:2]1[CH2:8][O:7][C:5](=[O:6])[CH2:4]1.[OH:3][CH:2]([CH2:1][OH:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 12674Dimethyl malateHCID 183021,2,4-Butanetriol

Product 2

HCID 956523,4-Dihydroxybutanoic acid gamma-lactoneHCID 2735094Methyl 3,4-dihydroxybutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[Ru(CH3CN)3(triphos)](CF3SO3)2 (11.5 mg), dimethyl DL-malate (0.65 g), and 1.0 ml of methanol were added into a 20-ml Schlenk tube under an argon atmosphere, and the mixture was stirred for 5 minutes at room temperature. This liquid was transferred to a 100-ml autoclave having a stirrer placed inside, under an argon atmosphere. The autoclave was purged with hydrogen, and then hydrogen was further included in the autoclave up to 4.0 MPa. The contents of the autoclave were heated and stirred at 100° C. for 14 hours. After cooling, the reaction liquid was analyzed by gas chromatography, and it was found that 1,2,4-butanetriol was produced at a yield of 30.6%, β-hydroxy-γ-butyrolactone at a yield of 42.3%, and methyl 3,4-dihydroxybutanoate at a yield of 21.4%.

Workup

  1. customThe autoclave was purged with hydrogen
  2. temperatureThe contents of the autoclave were heated
  3. stirringstirred at 100° C. for 14 hours
  4. temperatureAfter cooling
  5. customthe reaction liquid

Sources & evidence

ORD record
ord-2c03c283bf614cd99d0f8ce54dcd358e
Source dataset
uspto-grants-2011_09
Patent number
US08013193B2

Linked notes

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