Water → 3-(2-Chloro-4-cyanophenyl)propanol

HRID 68028Notes

Reaction equation

HRID 68028 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12](O)=[O:13].[H]1[BH2][H][BH2]1.O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 962WaterHCID 130420963-(2-Chloro-4-cyanophenyl)propanoic acid

Product 1

HCID 130420973-(2-Chloro-4-cyanophenyl)propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3-(2-chloro-4-cyanophenyl)-propanoic acid (14.3 g, 0.068 mol) in 70 mL of dry THF at -18° C. was added B2H6 (72 ml, 0.068 mol) in THF. The mixture was stirred at room temperature overnight. After addition of water, the layers were separated and the aqueous phase was extracted with ether. Evaporation and distillation gave 3-(2-chloro-4-cyanophenyl)propanol as an oil: 11.0 g; bp 55°-60° C. (0.005 mm Hg). Anal. calcd for C10H10ClNO: C, 61.39; H, 5.15; N, 7.16. Found: C, 61.02; H, 5.19; N, 6.76.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous phase was extracted with ether
  3. customEvaporation and distillation

Sources & evidence

ORD record
ord-9612dc692cdc459a8cbe8cc3dd553fcb
Source dataset
uspto-grants-1982_08
Patent number
US04347382

Reaction notes

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