HCID 14721899, compound → HCID 14721900, compound

HRID 1084812Notes

Reaction equation

HRID 1084812 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[C:8](=[O:20])[CH2:9][C:10]([CH3:19])([CH3:18])[CH2:11][C:12]=2[O:13][CH2:14]C(C)C)=[CH:4][CH:3]=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:8](=[O:20])[CH2:9][C:10]([CH3:19])([CH3:18])[CH2:11][C:12]=2[O:13][CH3:14])=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 14721899HCID 14721899, compound

Product 1

HCID 14721900HCID 14721900, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 154 g of the 2-(4-chlorobenzyl)-3-(2-methylpropoxy)-5,5-dimethylcyclohex-2-en-1-one obtained in Example 1 in 1200 ml methanol containing 3 g p-toluenesulphonic acid was refluxed for 2 hours. The reaction mixture was then extracted with 3 liters water and 1 liter diethyl ether and re-extracted with a further 1 liter diethyl ether. The organic phases were then back-washed first with 200 ml 10% aqueous sodium hydroxide and then with 100 ml saturated sodium chloride solution, dried over anhydrous magnesium sulphate and flashed. The residue was then crystallised in 60/80 petroleum, filtered and air-dried to give 98 g 2-(4-chlorobenzyl)-3-methoxy-5,5-dimethylcyclohex-2-en-1-one as a white solid, m.pt. 62°-63° C. Yield: 73%.

Workup

  1. extractionThe reaction mixture was then extracted with 3 liters water and 1 liter diethyl ether
  2. extractionre-extracted with a further 1 liter diethyl ether
  3. washThe organic phases were then back-washed first with 200 ml 10% aqueous sodium hydroxide
  4. dry with materialwith 100 ml saturated sodium chloride solution, dried over anhydrous magnesium sulphate
  5. customThe residue was then crystallised in 60/80 petroleum
  6. filtrationfiltered
  7. customair-dried

Sources & evidence

ORD record
ord-ca0e1157e6e5445cb52fbc6f1264a26a
Source dataset
uspto-grants-1991_04
Patent number
US05006552

Reaction notes

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