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

HRID 72854
Notes
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Reaction equation

HRID 72854 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[Li][CH2:13]CCC.[OH:17][C:18]1([CH3:25])[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1>COCCOC>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:21]1[CH2:22][CH2:23][C:18]([O:17][CH3:13])([CH3:25])[CH2:19][CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 285394-Hydroxy-4-methylcyclohexanoneHCID 80029Trimethyl phosphonoacetateHCID 178418339Butyllithium

Product 1

HCID 66742062(4-Methoxy-4 methyl-cyclohexylidene)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
0 °C

Procedure

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%).

Workup

  1. stirringthe mixture stirred 2.5 hours at 0° C. until TCL
  2. customcomplexion of the reaction
  3. customProduct was obtained
  4. extractionafter extraction with dichloromethane (7.71 g, 69%)

Sources & evidence

ORD record
ord-d765b0a07c0e4665acc96698a2b2a4ee
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829029B2

Reaction notes

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