Acetyl chloride → HCID 10313197, compound

HRID 1867920Notes

Reaction equation

HRID 1867920 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[C:8](Cl)(=[O:10])[CH3:9].C([O-])([O-])=O.[K+].[K+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:8]([O:1][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 10313197HCID 10313197, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of racemic α-hydroxy-γ-butyrolactone (25 g; 0.25 mol), DMAP (1.5 g), acetylchloride (25.5 ml; 0.37 mol) in CH2Cl2 (325 mL) was added solid K2CO3 (50 g) in portions (slightly exothermic). The reaction mixture was stirred at room temperature overnight, filtered and evaporated to dryness. Column chromatography (Petrol ether 80-100:EtOAc=2:1) gave 26.4 g (75%) racemic α-acetoxy-γ-butyrolactone.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-1c37d22bebb14626abdc9e848295ac25
Source dataset
uspto-grants-2009_12
Patent number
US07632948B2

Reaction notes

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