Acetic Acid → HCID 66640999, compound

HRID 1093939Notes

Reaction equation

HRID 1093939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:6]=[C:5]([O:14][CH3:15])[C:4]=1[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[C:22]([O:24][CH3:25])=[O:23].[Na].C(O)(=O)C>CO.O>[CH3:15][O:14][C:5]1[CH:6]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 59864405HCID 59864405, compound

Product 1

HCID 66640999HCID 66640999, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

600 mg (1.7 mmol) of methyl 2-(2,6-dimethoxy-4-pentylphenyl)cyclohexane-carboxylate were dissolved in 10 ml of methanol, a solution of 200 mg (8.7 mmol) of sodium in 7.5 ml of methanol was added, and the mixture was heated under reflux overnight. The mixture was subsequently diluted with water, acidified using acetic acid and extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and evaporated, giving 388 mg (75%) of methyl trans-2-(2,6-dimethoxy-4-pentyl-phenyl)cyclohexanecarboxylate as a colourless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8f018cdb39f0453ea014aeeac3242108
Source dataset
uspto-grants-2012_03
Patent number
US08133887B2

Reaction notes

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