Potassium Hydroxide → 744162-52-5

HRID 261106노트

반응식

HRID 261106 반응식
C[O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][CH:8]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[CH2:11][CH2:10][N:9]2[CH3:18])=[CH:5][CH:4]=1.[OH-].[K+]>C(O)COCCO>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[CH2:11][CH2:10][N:9]2[CH3:18])=[CH:19][CH:20]=1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 3562281-(4-Methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline

생성물 1

HCID 2762941744162-52-5수율 72%

시약·촉매·용매 1

HCID 8117Diethylene Glycol용매

실험 절차

A mixture of 253.9 g (0.935 mol) of (-)-1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline and 1.2 l. of diethylene glycol was warmed to 80°-100° and 260 g of potassium hydroxide (85% A.C.S. grade) was added. The reaction mixture was heated to 210° and stirred at this temperature under a constant stream of nitrogen for 36 hours. During this period, time to time the stop cock was removed to allow escape of water vapor. If this is not done, the desired inner temperature of 210° cannot be attained. The dark brown solution was cooled to room temperature and diluted with water (600 ml) and extracted with ether (400 ml). The aqueous solution was made acidic with concentrated aqueous hydrochloric acid and then basified with concentrated aqueous ammonium hydroxide. The aqueous suspension was extracted with ethyl acetate (4×250 ml). The ethyl acetate solution was washed with water and dried. Removal of the solvent gave 172.5 g (72%) of crude (-)-1-(p-hydroxybenzyl)-2-methyl- 1,2,3,4,5,6,7,8-octahydroisoquinoline. For analysis, a sample of this compound was recrystallized from tetrahydrofuran-heptane, mp 119°-120°, [α]25D-36.01° (c 0.98, MeOH).

후처리

  1. temperatureThe reaction mixture was heated to 210°
  2. waitDuring this period
  3. customtime to time the stop cock was removed
  4. custominner temperature of 210°
  5. additiondiluted with water (600 ml)
  6. extractionextracted with ether (400 ml)
  7. extractionThe aqueous suspension was extracted with ethyl acetate (4×250 ml)
  8. washThe ethyl acetate solution was washed with water
  9. customdried
  10. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-e1dc6bb3db78401488b97c74a72f4f68
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04163853

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