Thionyl Chloride → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 722451ノート

反応式

HRID 722451 の反応式
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

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 4379756Sodium 4-hydroxybenzenesulfonate

生成物 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chloride収率 98.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c2302c81c6544f9ea17489e21660dc2a
出典データセット
uspto-grants-2006_11
特許番号
US07138432B1

反応ノート

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