Chlorosulfonic acid → 2-(Octyloxy)-5-(2,4,4-trimethylpentan-2-yl)benzene-1-sulfonyl chloride

HRID 620707Notes

Reaction equation

HRID 620707 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:17])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:24][S:25](O)(=[O:27])=[O:26].P(Cl)(Cl)(Cl)=O>ClCCl>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH2:19][C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:18])[CH3:17])=[CH:12][C:11]=1[S:25]([Cl:24])(=[O:27])=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 24813Phosphorus oxychlorideHCID 212440051-(Octyloxy)-4-(2,4,4-trimethylpentan-2-yl)benzene

Product 1

HCID 146183222-(Octyloxy)-5-(2,4,4-trimethylpentan-2-yl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 900 ml of dichloromethane was dissolved 159 g of Compound A and the solution was stirred while cooling with an ice bath. After slowly adding dropwise 41.5 ml of chlorosulfonic acid to the solution, the mixture was stirred for 1.5 hours. Then, dichloromethane was removed while reducing the pressure by a tap aspirator and 480 ml of N,N-dimethylacetamide and 150 ml of acetonitrile were added to the residue formed. After adding dropwise 93.2 ml of phosphorous oxychloride to the mixture over a period of 40 minutes, the resultant mixture was stirred for 1.5 hours at 40° C. The solution was extracted four times with 500 ml of hexane and the hexane layer was collected and concentrated to provide 229 g of a crude product of 2-octyloxy-5-t-octylbenzenesulfonyl chloride (Compound B). The crude product was used as it was in the subsequent reaction.

Workup

  1. temperaturewhile cooling with an ice bath
  2. stirringthe mixture was stirred for 1.5 hours
  3. customThen, dichloromethane was removed
  4. additionwere added to the residue
  5. customformed
  6. extractionThe solution was extracted four times with 500 ml of hexane
  7. customthe hexane layer was collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c84f2476c4ba48c59a07deaeca7e2759
Source dataset
uspto-grants-1989_04
Patent number
US04822730

Reaction notes

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