Toluene → HCID 67179295, compound

HRID 1045067Notes

Reaction equation

HRID 1045067 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1([CH3:16])[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C1(P(=[CH:36][C:37]([O:39][CH3:40])=[O:38])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:40][O:39][C:37](=[O:38])[CH:36]=[C:12]1[CH2:13][CH2:14][C:9]([CH3:16])([CH3:8])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 138166Cyclohexanone, 4,4-dimethyl-

Product 1

HCID 67179295HCID 67179295, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a toluene (5 mL) solution containing 4,4-dimethyl-cyclohexanone (500 mg, 4.0 mmol) was added methyl (triphenylphosphoranylidene)acetate (2.0 g, 6.0 mmol) and the reaction was heated to 60-70° C. for 48 h. The reaction was monitored by TLC. The reaction was cooled to room temperature, diluted with dichloromethane, washed with water, concentrated under vacuum, and the crude product was purified on a silica gel column to afford (4,4-dimethyl-cyclohexylidene)-acetic acid methyl ester (100 mg, 14% yield).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water
  3. concentrationconcentrated under vacuum
  4. customthe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-34fbe80e1a2047908d5328fced50b0da
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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