Chloroform → Ethyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylate

HRID 2051444Notes

Reaction equation

HRID 2051444 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][CH3:20])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(Cl)(Cl)Cl.B.[Na]>C(O)C>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14401906Ethyl 4-(4-acetylphenyl)benzoateHCID 178418435HCID 178418435, compound

Product 1

HCID 14425758Ethyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

32.2 g (0.12 mol) of ethyl 4'-acetyl-4-biphenylcarboxylate, 150 ml of chloroform and 50 ml of ethanol were supplied into a four-necked flask provided with a stirrer and a thermometer. Then 2.3 g (0.06 mol) of sodium boron hydride was added at 15°-25° C. over a period of 10 minutes. The mixture was maintained at the same temperature for 2 hours and the resulting reaction solution 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 form 30.8 g (95% yield) of ethyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylate (III-5).

Workup

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

Sources & evidence

ORD record
ord-b025d54b273a475f9867bac39585baba
Source dataset
uspto-grants-1991_05
Patent number
US05019298

Reaction notes

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