Phosphorus pentachloride → 4-Cyclohexylbenzene-1-sulfonyl chloride

HRID 34884

Reaction equation

HRID 34884 reaction equation
[Na+].[CH:2]1([C:8]2[CH:13]=[CH:12][C:11]([S:14]([O-:17])(=O)=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.P(Cl)(Cl)(Cl)(Cl)[Cl:19]>>[CH:2]1([C:8]2[CH:13]=[CH:12][C:11]([S:14]([Cl:19])(=[O:17])=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 236948934-Cyclohexylbenzenesulfonic Acid Sodium Salt

Product 1

HCID 43394424-Cyclohexylbenzene-1-sulfonyl chloride

Conditions

Temperature
70 °C

Procedure

The sodium salt prepared in Example I (420 gm, 1.6M) is intermittently mixed with phosphorous pentachloride (160 gm, 0.77M) in a three liter multi-necked flask and slowly warmed to 70° C. in an oil bath. The liquified reaction mass is aged at 70° C. for 8 hours, then cooled to room temperature and carefully poured over one kilogram of cracked ice. A solid precipitate is removed by filtration and the aqueous phase is extracted with methylene chloride three times, each time using 300 milliliters of MeCl. The combined organic phases are dried and concentrated using a rotary evaporator. 4-cyclohexylbenzenesulfonyl chloride (338 gm, 81% of theoretical yield) was recovered as a crude product.

Workup

  1. customThe liquified reaction mass
  2. temperaturecooled to room temperature
  3. customA solid precipitate is removed by filtration
  4. extractionthe aqueous phase is extracted with methylene chloride three times
  5. customThe combined organic phases are dried
  6. concentrationconcentrated
  7. customa rotary evaporator
  8. custom4-cyclohexylbenzenesulfonyl chloride (338 gm, 81% of theoretical yield) was recovered as a crude product

Sources & evidence

ORD record
ord-3edceb04c1ea4df588859da19aabf28a
Source dataset
uspto-grants-1988_08
Patent number
US04764239

Linked notes

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