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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 72854Generated: October 25, 2026

4-Hydroxy-4-methylcyclohexanone → (4-Methoxy-4 methyl-cyclohexylidene)-acetic acid methyl ester

https://huagongshe.com/reaction/72854

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Hydroxy-4-methylcyclohexanoneHCID 28539—
ReactantTrimethyl phosphonoacetateHCID 80029—
ReactantButyllithiumHCID 178418339—
Solvent1,2-DimethoxyethaneHCID 8071—
Product(4-Methoxy-4 methyl-cyclohexylidene)-acetic acid methyl esterHCID 66742062—

Reaction Conditions

Temperature0 °C

Reaction Steps

A mixture of trimethyl phosphonoacetate (9.11 mL, 56 mmol) and (40 mL, 64 mmol) of n-BuLi (1.6N) in DME (60 mL) is stirred for 10 minutes at 0° C. 4-Hydroxy-4-methyl-cyclohexanone (8 g, 56 mmol) was added and the mixture stirred 2.5 hours at 0° C. until TCL indicated complexion of the reaction. Product was obtained after extraction with dichloromethane (7.71 g, 69%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829029B2
Source datasetuspto-grants-2014_09
ORD IDord-d765b0a07c0e4665acc96698a2b2a4ee
Source noteuspto-grants-2014_09