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

HRID 67868Notes

Reaction equation

HRID 67868 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. ##STR31##

Workup

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

Sources & evidence

ORD record
ord-062da8e8cd664b9e8317e28b82d1db57
Source dataset
uspto-grants-1982_08
Patent number
US04347177

Reaction notes

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