Hydrochloric Acid → Dihydroanisoin

HRID 2253941

Reaction equation

HRID 2253941 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[OH:12])=[O:10])=[CH:5][CH:4]=1.[BH4-].[Na+].Cl>C(O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:11]([OH:12])[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[OH:10])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 954154,4'-DimethoxybenzoinHCID 4311764Sodium borohydride

Product 1

HCID 160757DihydroanisoinYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 3 liters of dry ethanol, 75 g of 4,4'-bismethoxybenzoin and 21 g of sodium borohydride were refluxed for 2 hours. After adding 250 ml of concentrated hydrochloric acid to the reaction mixture, the resulting mixture was poured into 1300 ml of ice water, followed by filtration of deposited crystals. After recrystallized from 95% ethanol, there was obtained 57 g of 1,2-di(p-methoxyphenyl)ethane-1,2-diol, which was then added to 570 ml of 80% acetic acid and stirred at 90° C. for 50 minutes. Then, the reaction mixture was poured into 4 liters of ice water and deposited crystals were filtered. After drying, the crystals were recrystallized from isopropyl ether to give 40 g of Compound (e) in 69% yield.

Workup

  1. filtrationfollowed by filtration of deposited crystals
  2. customAfter recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-f20d4f06dddb4b29a99091583940995d
Source dataset
uspto-grants-1993_08
Patent number
US05233089

Linked notes

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