Thionyl Chloride → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 722451노트

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HRID 722451 반응식
S(Cl)([Cl:3])=O.[Na+].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:16])(=O)=[O:14])=[CH:9][CH:8]=1>C(Cl)Cl.CN(C=O)C>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([Cl:3])(=[O:16])=[O:14])=[CH:9][CH:8]=1

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 4379756Sodium 4-hydroxybenzenesulfonate

생성물 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chloride수율 98.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

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온도
65 °C

실험 절차

A solution of 31.4 ml (430 mmol) of thionyl chloride and 0.2 ml (2.58 mmol) of DMF was quickly added to 10 g (43 mmol) of 4-hydroxybenzenesulfonic acid sodium salt under N2 atmosphere. The resulting mixture is stirred at 65° C. for 6 h. At the end of this time, the mobile, nearly homogenous reaction mixture is poured on ice with vigorous stirring. An oily lower layer is produced and which is dissolved in 100 ml of CH2Cl2. The aqueous layer is extracted with CH2Cl2 and the combined organic solution is dried over MgSO4 and concentrated under reduced pressure to give 8.19 g of 4-hydroxybenzenesulfonyl chloride; NMR (CDCl3): 5.3 (br s, 1H), 7.01 (d, 2H, J=9.08 Hz), 7.94 (d, 2H, J=9.08 Hz).

후처리

  1. additionAt the end of this time, the mobile, nearly homogenous reaction mixture is poured on ice with vigorous stirring
  2. customAn oily lower layer is produced
  3. extractionThe aqueous layer is extracted with CH2Cl2
  4. dry with materialthe combined organic solution is dried over MgSO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c2302c81c6544f9ea17489e21660dc2a
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138432B1

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