2,4-Dichlorophenol → Dichloromethane

HRID 637520Notes

Reaction equation

HRID 637520 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Cl:10][S:11](O)(=[O:13])=[O:12]>O>[OH:9][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[S:11]([Cl:10])(=[O:13])=[O:12].[CH2:6]([Cl:8])[Cl:10]

Participants

5

Reactant 2

HCID 84492,4-DichlorophenolHCID 24638Chlorosulfonic acid

Product 2

HCID 6344DichloromethaneYield 81%HCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
24 °C

Procedure

Molten 2,4-dichlorophenol (164.27 g) was added to 332 ml of chlorosulfonic acid at 36°-40° C. over one and one-half hours. After a 10 minute hold period at 38°-40° C. the reaction mixture was cooled to 24° C. and held for 1 hour. This solution was then pumped into 500 ml of water which had been cooled to 5° C. External cooling was required to maintain the quench slurry at 60° C. Once the quench was complete, the slurry was cooled to 45° C. and the agitation was stopped to allow the solids to settle. Using a dipstick, 380 ml of supernatent was removed. This volume was replaced with 180 ml H2O and 200 ml CH2Cl2. The organic layer was separated and a second 50 ml wash with CH2Cl2 was obtained and combined with the first to provide 340 ml, 489 g of a 40.3% solution of (C) in CH2Cl2 (81% yield).

Workup

  1. waitheld for 1 hour
  2. temperaturehad been cooled to 5° C
  3. temperatureExternal cooling
  4. temperatureto maintain the quench slurry at 60° C
  5. temperaturethe slurry was cooled to 45° C.
  6. customwas removed
  7. customThe organic layer was separated
  8. washa second 50 ml wash with CH2Cl2
  9. customwas obtained

Sources & evidence

ORD record
ord-adcb5bb6ef674b34b455f93e31c16af3
Source dataset
uspto-grants-1985_12
Patent number
US04556733

Reaction notes

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