Water → 3-(3-Chloro[1,1'-biphenyl]-2-yl)propan-1-ol

HRID 1388825Notes

Reaction equation

HRID 1388825 reaction equation
[Cl:1][C:2]1[C:3]([CH:14]([CH3:18])C(O)=O)=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.O.[O:20]1CCC[CH2:21]1>>[Cl:1][C:2]1[C:3]([CH2:14][CH2:18][CH2:21][OH:20])=[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 20403362HCID 20403362, compound

Product 1

HCID 204033423-(3-Chloro[1,1'-biphenyl]-2-yl)propan-1-ol

Procedure

Under a dry argon atmosphere, borane-tetrahydrofuran complex (230 ml of a 1.5 M solution in tetrahydrofuran) was added dropwise to a stirred solution of (3-chloro[1,1'-biphenyl]-2-ylpropanoic acid (40.0 g, 0.15 mole) in tetrahydrofuran (250 ml). The reaction mixture was stirred at room temperature for approximately 18 hours. Water (30 ml) was then added to the reaction mixture during a 0.5 hour period. The solvent was removed from the mixture under reduced pressure to yield an oil. The oil was partitioned betwen methylene chloride and dilute aqueous sodium hydroxide. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to yield 3-(3-chloro[1,1'-biphenyl]-2-yl)-1-propanol as an oil.

Workup

  1. customThe solvent was removed from the mixture under reduced pressure
  2. customto yield an oil
  3. customThe oil was partitioned betwen methylene chloride and dilute aqueous sodium hydroxide
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-b191f784274943cc941e99f8391fd803
Source dataset
uspto-grants-1984_02
Patent number
US04433182

Reaction notes

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