Hydrochloric Acid → 1-Phenylethanol, (R)-

HRID 1604723Notes

Reaction equation

HRID 1604723 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1([SiH2]C2C=CC=CC=2)C=CC=CC=1.CO.Cl>O1CCCC1>[C:4]1([C@H:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7410Acetophenone2×HCID 69888Diphenylsilane

Product 1

HCID 6375161-Phenylethanol, (R)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving a mixed solution of 0.25 mmol of [Rh(COD)Cl]2, 0.0005 mmolof(4S,4'S)-2,2'-bis(o-diarylphosphinophenyl)-4,4, 5,5'-tetrahydro-4,4'-bi(1,3-oxazole) prepared in Example 1 and 1 mmol acetophenone in 1 ml of tetrahydrofuran, the solution was stirred for an hour at room temperatures. At 0 ° C., 1 mmol of acetophenone and 1.5 mmol of diphenylsilane were added to the mixture. After the reaction mixture was stirred for 7 hours at 0° C., 5 ml of methanol and 10 ml of 0.1 N HCl aqueous solution were added. After the organic layer was extracted with diethyl ether and dried (Na2SO4), solvent was removed by vacuum distillation. The remainder was purified by using a silica column chromatography to obtain an optically active secondary alcohol, (R)-1-phenyl ethyl alcohol.

Workup

  1. stirringAfter the reaction mixture was stirred for 7 hours at 0° C.
  2. extractionAfter the organic layer was extracted with diethyl ether
  3. dry with materialdried (Na2SO4), solvent
  4. customwas removed by vacuum distillation
  5. customThe remainder was purified

Sources & evidence

ORD record
ord-612bfc13956546a6884f14579d7b3660
Source dataset
uspto-grants-1999_11
Patent number
US05994556

Reaction notes

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