alpha-Cyclohexylphenylacetic acid → β-Cyclohexylbenzeneethanol

HRID 375285Notes

Reaction equation

HRID 375285 reaction equation
[C:1]1([CH:7]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.CSC>O1CCCC1>[CH:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][OH:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 97942alpha-Cyclohexylphenylacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 3610110β-Cyclohexylbenzeneethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 500 mL round-bottomed flask equipped with condenser and N2 inlet were added 15 g (68.8 mmol) α-phenylcyclohexylacetic acid, 110 mL dry tetrahydrofuran, and 137 mL (275 mmol) of a 2M solution of borane-methyl sulfide in tetrahydrofuran. The solution was refluxed 60 hr, cooled, and evaporated. The residue was taken up carefully in 200 mL ethanol, treated with 2 g sodium carbonate, and refluxed 3 hr. The reaction was cooled, evaporated, taken up in ethyl acetate/water, separated, and the aqueous phase extracted with fresh ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, and evaporated to an oil which solidified on standing. The yield was 12.27 g (87%).

Workup

  1. customTo a 500 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe solution was refluxed 60 hr
  3. temperaturecooled
  4. customevaporated
  5. additiontreated with 2 g sodium carbonate
  6. temperaturerefluxed 3 hr
  7. temperatureThe reaction was cooled
  8. customevaporated
  9. customseparated
  10. extractionthe aqueous phase extracted with fresh ethyl acetate
  11. washwashed with brine
  12. dry with materialdried over sodium sulfate
  13. customevaporated to an oil which

Sources & evidence

ORD record
ord-765200506d054ee7b435fd4935bb3e14
Source dataset
uspto-grants-1996_01
Patent number
US05484917

Reaction notes

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