4-tert-Butylcyclohexanone → (4-tert-Butylcyclohexylidene)acetic acid methyl ester

HRID 2268749Notes

Reaction equation

HRID 2268749 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:12][O:13][C:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15]>C1(C)C=CC=CC=1>[CH3:12][O:13][C:14](=[O:15])[CH:16]=[C:8]1[CH2:9][CH2:10][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 73924-tert-ButylcyclohexanoneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 10750958(4-tert-Butylcyclohexylidene)acetic acid methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-tert-Butylcyclohexanone (8.62 g, 56 mmol) was dissolved in toluene (200 ml). Methoxycarbonylmethylenetriphenylphosphorane (56.1 g, 168 mmol) was added with stirring and the reaction mixture was heated under reflux for 3 days. The solvent was removed in vacua. The residue was dissolved in hot hexanes (100 ml) and cooled to room temperature. The precipitate was filtered off and the filtrate was evaporated in vacuo to afford a yellow oil which was then purified by chromatography (silica gel, hexane/ethyl acetate, 2:1 as eluant) to give the title compound as an oil (10.78 g, 92%). 1H-NMR; δ (CDCl3) 5.60 (1H, s), 3.87 (1H, m), 3.69 (3H, s), 2.38-2.10 (2H, m), 2.03-1.77 (3H, m), 1.36-1.02 (3H, m) and 0.87 (9H, s).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3 days
  3. customThe solvent was removed in vacua
  4. dissolutionThe residue was dissolved in hot hexanes (100 ml)
  5. filtrationThe precipitate was filtered off
  6. customthe filtrate was evaporated in vacuo
  7. customto afford a yellow oil which
  8. customwas then purified by chromatography (silica gel, hexane/ethyl acetate, 2:1 as eluant)

Sources & evidence

ORD record
ord-932310a3fc7a4940abc23daa890f1fff
Source dataset
uspto-grants-2001_12
Patent number
US06329373B1

Reaction notes

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