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Ethanol → 4-(Docosyloxy)-alpha-[4-(docosyloxy)phenyl]benzenemethanamine

HRID 1025057
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인쇄 미리보기

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HRID 1025057 반응식
[CH2:1]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([NH:60]C(=O)OCC)[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C1(C)C=CC=CC=1.C(O)C.[OH-].[Na+]>C(OCC)(=O)C.CCCCCC.O>[CH2:1]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH:30]([NH2:60])[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[CH:33][CH:32]=2)=[CH:28][CH:29]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]
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참가 물질

8

반응물 4

HCID 702EthanolHCID 1140TolueneHCID 14798Sodium Hydroxide2회HCID 86646200Ethyl di(4-docosoxyphenyl)methylcarbamate

생성물 1

HCID 665753054-(Docosyloxy)-alpha-[4-(docosyloxy)phenyl]benzenemethanamine수율 98%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To crude crystals (31.9 g) of ethyl di(4-docosoxyphenyl)methylcarbamate were added toluene (300 mL), ethanol (200 mL), and sodium hydroxide (4.2 g, 105 mmol), and the mixture was refluxed under stirring at 100° C. Sodium hydroxide (total 9.8 g, 245 mmol) was added, and the mixture was stirred for 16 hours. The reaction mixture was cooled to room temperature, and water (300 mL), hexane (200 mL) and ethyl acetate (200 mL) were added for partitioning. The aqueous layer was discarded, and the organic layer and precipitated crystals were washed with water (300 mL×2). The organic layer and crystals were recovered. The solvent was evaporated under reduced pressure. To the residue were added water (150 mL) and acetonitrile (150 mL) to allow crystallization. The crystals were collected by filtration and thoroughly washed with water and acetonitrile to give di(4-docosoxyphenyl)methylamine (28.1 g, 33.7 mmol, 98% vs —OH).

후처리

  1. temperaturethe mixture was refluxed
  2. stirringthe mixture was stirred for 16 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customfor partitioning
  5. customthe organic layer and precipitated crystals
  6. washwere washed with water (300 mL×2)
  7. customThe organic layer and crystals were recovered
  8. customThe solvent was evaporated under reduced pressure
  9. additionTo the residue were added water (150 mL) and acetonitrile (150 mL)
  10. customcrystallization
  11. filtrationThe crystals were collected by filtration
  12. washthoroughly washed with water and acetonitrile

출처 및 근거

ORD 기록
ord-1a079cd4ef834509905c6c1633bd19e8
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722934B2

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