Reaction #1755

ord-d5a8195f23794884af3a23a8c8f6148d

Reaction equation

O
water
CC(=O)O[C@H]1CC[C@H](c2ccc(CCl)cc2)CC1
trans-O-acetyl-4-(4-chloromethylphenyl)-cyclohexanol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCNCC
diethylamine
→
CCN(CC)Cc1ccc([C@H]2CC[C@H](OC(C)=O)CC2)cc1
trans-O-Acetyl-4-(4-diethylaminomethylphenyl)-cyclohexanol

Reactants

O
water
CC(=O)O[C@H]1CC[C@H](c2ccc(CCl)cc2)CC1
trans-O-acetyl-4-(4-chloromethylphenyl)-cyclohexanol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCNCC
diethylamine

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Temperature
50°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionthe mixture is extracted with methylene chloride
  2. 2
    OtherThe organic phase is dried
  3. 3
    Otherevaporated down in vacuo
  4. 4
    Otherthe residue remaining is purified by column chromatography (aluminium oxide basic, activity stage III, ICN; petroleum ether/ethyl acetate=15:1)

Procedure

A solution of 1 g (3.75 mmol) of trans-O-acetyl-4-(4-chloromethylphenyl)-cyclohexanol in 10 ml of dimethylformamide is mixed with 0.52 g (3.75 mmol) of potassium carbonate and 0.27 g (3.75 mmol) of diethylamine. This mixture is heated to 50° C. for 6 hours with stirring, then water is added and the mixture is extracted with methylene chloride. The organic phase is dried, evaporated down in vacuo and the residue remaining is purified by column chromatography (aluminium oxide basic, activity stage III, ICN; petroleum ether/ethyl acetate=15:1). Colourless oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726205uspto-grants-1998_03