Potassium Hydroxide → 744162-52-5

HRID 1732810ノート

反応式

HRID 1732810 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 2762941744162-52-5収率 72%

試薬・触媒・溶媒 1

HCID 8117Diethylene Glycol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-45780caa3ff44f11aca50ecaf3a6a956
出典データセット
uspto-grants-1980_12
特許番号
USRE030452

反応ノート

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