Methanol → 6-(4'-Chloro-phenyl)-6-oxo-4-chloro-3,3-dimethyl-hexanoic acid methyl ester

HRID 2295481Notes

Reaction equation

[CH3:1][C:2]1([CH3:18])[CH:7]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:10])O[C:4](=[O:5])[CH2:3]1.[CH3:19][OH:20].S(Cl)([Cl:23])=O>>[CH3:19][O:20][C:4](=[O:5])[CH2:3][C:2]([CH3:18])([CH3:1])[CH:7]([Cl:23])[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:10]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 204745093,3-Dimethyl-4-(4'-chloro-phenacyl)-gamma-butyrolactone

Product 1

HCID 541160596-(4'-Chloro-phenyl)-6-oxo-4-chloro-3,3-dimethyl-hexanoic acid methyl ester

Conditions

Temperature: 50 °C

Procedure

134 g of 3,3-dimethyl-4-(4'-chloro-phenacyl)-γ-butyrolactone were dissolved in 215 g of thionyl chloride in a 0.7 liter autoclave with a glass liner. 100 g of methanol were then pumped in and the mixture was heated to 50° C. for 4 hours. After working up as in Example 10, 6-(4'-chloro-phenyl)-6-oxo-4-chloro-3,3-dimethyl-hexanoic acid methyl ester was obtained.

Sources & evidence

ORD record: ord-1de28fd63cad4bea9b15e7d13b28bc1c
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04425282

Reaction notes

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