Thionyl Chloride → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 1662979Notes

Reaction equation

HRID 1662979 reaction equation
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

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 4379756Sodium 4-hydroxybenzenesulfonate

Product 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chlorideYield 98.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-068838e3fbfd42e8aae1aa1657413df5
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

Loading…