Citric Acid → HCID 57433661, compound

HRID 2080684Notes

Reaction equation

HRID 2080684 reaction equation
[C:1]([O:4][CH:5]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][C:7](O)=[O:8])(=[O:3])[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:4][CH:5]([CH2:6][CH2:7][OH:8])[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 11769311METHYL 2-ACETOXY-3-CARBOXYPROPANOATE

Product 1

HCID 57433661HCID 57433661, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g of dl-maleic acid was dissolved in 20 ml of acetyl chloride, and stirred under heat at 45° C. for 3 hours. Acetyl chloride was evaporated away under reduced pressure, the resulting crude product was dissolved in 30 ml of methanol, and stirred overnight. The solvent was evaporated away under reduced pressure to obtain 5.3 g of 3-(acetyloxy)-4-methoxy-4-oxobutanoic acid as a pale yellow oil. In an ice bath, 10 ml of borane-dimethylsulfide complex (10 M) was added to a tetrahydrofuran (25 ml) solution of 5.3 g of 3-(acetyloxy)-4-methoxy-4-oxobutanoic acid, and stirred at room temperature for 24 hours. Aqueous 10% citric acid was added to the reaction liquid, extracted with chloroform, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure to obtain 5.1 g of methyl 2-(acetyloxy)-4-hydroxybutanoate as a colorless transparent oil.

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated saline water
  3. customAfter dried
  4. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-3e31d940bde44f08b52a4e9737764ce5
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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