Hydrochloric Acid → Dihydroanisoin

HRID 2253941

반응식

HRID 2253941 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 160757Dihydroanisoin수율 75.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f20d4f06dddb4b29a99091583940995d
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05233089

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