Thionyl Chloride → 4-(Benzyloxy)benzene-1-sulfonyl chloride

HRID 2269328Notes

Reaction equation

HRID 2269328 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O-:18])(=O)=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].S(Cl)([Cl:22])=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([Cl:22])(=[O:18])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 22508374HCID 22508374, compound

Product 1

HCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a flask containing 4-Benzyloxy-benzenesulfonate, sodium salt (42.07 g) is added thionyl chloride (170 mL). This solution is treated with dimethyl formamide (0.5 mL) and is heated to 70° C. for 4 hours. The reaction is allowed to cool and is concentrated under reduced pressure then is diluted with ethyl acetate and washed with water (3 times) followed by three washes with saturated sodium bicarbonate and brine. The organic layer is dried over sodium sulfate and concentrated to give 4-Benzyloxy-benzenesulfonyl chloride as white solid (39.18 g).

Workup

  1. temperatureto cool
  2. concentrationis concentrated under reduced pressure
  3. additionthen is diluted with ethyl acetate
  4. washwashed with water (3 times)
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0eed60a0ff8491785c35cbecc2d64a3
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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