HCID 19771308, compound → HCID 19771310, compound

HRID 1589923Notes

Reaction equation

HRID 1589923 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]23[O:16][CH:8]2[C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH2:11][CH2:12]3)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9](=[O:15])[C:8]=2[OH:16])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 19771308HCID 19771308, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19771310HCID 19771310, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

38.7 g (146 mmol) 1-(4-chlorobenzyl)-1,2-epoxy-4,4-dimethylcyclohexan-3-one obtained in Example 2 above was added to a slurry of potassium tert-butoxide (33 g, 294 mmol) in tert-butanol (200 ml) at 40° C. The mixture was then warmed to 60 C and stirred for 2 hours before being cooled in ice and quenched with water (50 ml). 5M Hydrochloric acid (100 ml) was then added slowly followed by water (300 ml). The mixture was then cooled to 0° C., filtered and the residue washed with water (100 ml). Drying under vacuum at 40° C. gave 36.3 g 1-(4-chlorobenzyl)-2-hydroxy-4,4-dimethylcyclohex-1-en-3-one, m.pt. 80-82° C.

Workup

  1. temperatureThe mixture was then warmed to 60 C
  2. temperaturebefore being cooled in ice
  3. customquenched with water (50 ml)
  4. addition5M Hydrochloric acid (100 ml) was then added slowly
  5. filtrationfiltered
  6. washthe residue washed with water (100 ml)
  7. customDrying under vacuum at 40° C.

Sources & evidence

ORD record
ord-07453eefd598420b9d85ee4f9b8fb896
Source dataset
uspto-grants-1993_04
Patent number
US05200535

Reaction notes

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