Phosphoric Acid → HCID 14944829, compound

HRID 486844Notes

Reaction equation

HRID 486844 reaction equation
[CH3:1][C:2]1([CH3:14])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH2:9][CH:10]([OH:13])[CH2:11][Cl:12])[O:3]1.P(=O)(O)(O)O>CC(C)=O>[C:2]([O:3][CH:4]=[CH2:5])(=[O:7])[CH3:1].[CH3:1][C:2]1([CH3:14])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH2:9][CH:10]([OH:13])[CH2:11][Cl:12])[O:3]1

Participants

5

Reactant 2

HCID 1004Phosphoric AcidHCID 14944829HCID 14944829, compound

Product 2

HCID 7904Vinyl AcetateHCID 14944829HCID 14944829, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
28 °C

Procedure

A mixture of 0.9 g (3.43 mmol) of (±)-2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one, 0.9 g of Lipase PS, 150 ml of a 0.1M phosphoric acid buffer solution (pH 7.2) and 450 ml of acetone was stirred at 28° C. for 3 hours. After the product was extracted with ethyl acetate, the solvent was distilled off, and the residue was subjected to silica gel chromatography (an eluent of hexane:vinyl acetate=3:1), thereby obtaining 27 mg (yield 3%) of (-)-2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one [a compound having the formula (1) in which n was 1, X was Cl, Y was a hydrogen atom, and a substituent was present at the 6-position] and 0.48 g (yield 53%) of (-)-2,2-dimethyl-6-(3-chloro-2-acetoxypropyl)-1,3-dioxin-4-one [a compound having the formula (1) in which n was 1, X was Cl, Y was Ac, and a substituent was present at the 6-position].

Workup

  1. extractionAfter the product was extracted with ethyl acetate
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-14228dc72eba458d9143692dae6dc170
Source dataset
uspto-grants-1994_03
Patent number
US05292891

Reaction notes

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