3-Chloropropiophenone → 3-Chloro-1-phenylpropanol

HRID 1885570Notes

Reaction equation

HRID 1885570 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[BH4-].[Na+]>C(O)C>[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

4

Reactant 2

HCID 702953-ChloropropiophenoneHCID 4311764Sodium borohydride

Product 1

HCID 5720643-Chloro-1-phenylpropanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloropropiophenone (25.2 g) was dissolved in abs. ethanol (200 ml), NaBH4 (2.2 g) was slowly added and the mixture stirred overnight at R.T. The mixture was filtered and the filtrate evaporated to dryness. H2O was added and the solution extracted with ether, the ether phase dried (MgSO4) and evaporated. The resulting oil purified on silioagel CH2Cl2 as eluent giving 3-chloro-1-phenyl-1-propanol (compound 14), identified by 1H NMR.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. additionH2O was added
  4. extractionthe solution extracted with ether
  5. dry with materialthe ether phase dried (MgSO4)
  6. customevaporated
  7. customThe resulting oil purified on silioagel CH2Cl2 as eluent

Sources & evidence

ORD record
ord-4495d5180e95401a9398bf9de94bc133
Source dataset
uspto-grants-1992_09
Patent number
US05145870

Reaction notes

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