Ammonia → 2-(2-Mercaptobenzyl)phenol

HRID 1987479노트

반응식

HRID 1987479 반응식
C[S:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].N.[Na].[NH4+].[Cl-]>CCCCCC.C(OCC)(=O)C.C1COCC1>[SH:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 686436452-(2-(Methylthio)benzyl)phenol

생성물 1

HCID 686436382-(2-Mercaptobenzyl)phenol수율 71.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 0.68 g 2-(2-(methylthio)benzyl)phenol (I) (2.96 mmol) in 4 ml freshly distilled THF at −78° C. was added 8 mL condensed ammonia followed by 0.15 g sodium. The blue solution was stirred for 2 hours at −78° C. before the mixture was warmed to ambient temperature. The reaction was allowed to stir overnight before NH4Cl was added until neutral. The mixture was extracted with ethyl acetate and the combined organic extracts washed with brine, dried over magnesium sulfate and concentrated. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.457 g product (2.12 mmol, 71% yield).

후처리

  1. temperaturewas warmed to ambient temperature
  2. additionwas added until neutral
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5f52a805e826418eab7d7b4187cbb477
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550505B2

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