Ethanol → HCID 14597164, compound

HRID 1729141Notes

Reaction equation

HRID 1729141 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(O)C.[BH4-].[Na+]>C(Cl)(Cl)Cl>[OH:3][CH:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 590101Benzyl 4-acetylbenzoateHCID 4311764Sodium borohydride

Product 1

HCID 14597164HCID 14597164, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

60.98 g (0.24 mol) of benzyl 4-acetylbenzoate (II-19), 100 ml of ethanol and 300 ml of chloroform were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 4.6 g (0.12 mol) of sodium borohydride was added at 15°-25° C., over a period of 10 minutes. The mixture was kept at the same temperature for 2 hours and the resulting 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 58.37 g (95% yield) of benzyl 4-(1-hydroxyethyl)phenylcarboxylate (III-19). nD25 =1.5682.

Workup

  1. customequipped with a stirrer
  2. customthe resulting reaction mixture
  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-040e794792b245c9934e2f35fd56165e
Source dataset
uspto-grants-1994_07
Patent number
US05332675

Reaction notes

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