Chloroform → HCID 14549130, compound

HRID 1729145Notes

Reaction equation

HRID 1729145 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(Cl)(Cl)Cl.[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 19011322HCID 19011322, compound

Product 1

HCID 14549130HCID 14549130, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

36.5 g (0.1 mol) of p-chlorobenzyl 4'-acetyl-4-biphenylcarboxylate, 150 ml of chloroform and 50 ml of ethanol were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 3.8 g (0.1 mol) of sodium borohydride was added at 15°-25° C. over a period of 10 minutes. The mixture was maintained at the same temperature for 2 hours. The reaction mixture was poured into ice-water and extracted twice with 200 ml of ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure to obtain 36.5 g (99.5% yield) of p-chlorobenzyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylate (III-27).

Workup

  1. customequipped with a stirrer
  2. temperatureThe mixture was maintained at the same temperature for 2 hours
  3. extractionextracted twice with 200 ml of ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-933186663b4647a79f2482b53a4bbaf0
Source dataset
uspto-grants-1994_07
Patent number
US05332675

Reaction notes

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