Hydrochloric Acid → HCID 54244847, compound

HRID 1196265Notes

Reaction equation

HRID 1196265 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C:21]([O-:24])(C)C.[K+].C(OCC)=O.Cl>C(O)(C)(C)C.O.C(OCC)(=O)C>[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:8][CH2:9][C:10](=[O:13])[CH:11]([CH:21]=[O:24])[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 1382814,4-DiphenylcyclohexanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 54244847HCID 54244847, compoundYield 107.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

4,4-Diphenylcyclohexanone (40 g) is added to a solution of potassium tert-butylate (66.5 g) in tert-butanol (500 cc), and a solution of ethyl formate (47.6 cc) in tert-butanol (500 cc) is then added dropwise. The reaction mixture is stirred at 50° C. for 8 hours, then cooled and diluted with water (3000 cc) and ethyl acetate (750 cc) and acidified to pH 2 with 4N hydrochloric acid. The aqueous phase is extracted with ethyl acetate (2×250 cc) and the combined organic phases are washed with water (250 cc) and saturated sodium chloride solution (250 cc), then dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). 4,4-Diphenyl-2-formylcyclohexanone (48 g) is obtained, and is used without purification for the next step of the synthesis.

Workup

  1. temperaturecooled
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×250 cc)
  3. washthe combined organic phases are washed with water (250 cc) and saturated sodium chloride solution (250 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-82e7a96350c84e6ab6bfa52f7acf00f3
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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