Methanesulfonyl chloride → 2-(2,4-Dichlorophenoxy)-1-propanol methanesulfonate

HRID 345574Notes

Reaction equation

HRID 345574 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH:5]([CH3:8])[CH2:6][OH:7].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(N(CC)CC)C>[CH3:14][S:15]([O:7][CH2:6][CH:5]([O:4][C:3]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=1[Cl:1])[CH3:8])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 3509832-(2,4-Dichlorophenoxy)propan-1-ol

Product 1

HCID 150969832-(2,4-Dichlorophenoxy)-1-propanol methanesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred mixture of 324 parts of 2-(2,4-dichlorophenoxy)-1-propanol and 700 parts of N,N-diethylethanamine were added dropwise at room temperature 335 parts of methanesulfonyl chloride (exothermic reaction: the temperature roses to reflux temperature). While cooling in a water-bath, stirring was continued for 30 minutes at room temperature. The reaction mixture was poured onto water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated. The residue was distilled by vacuum distillation, yielding 300 parts of 2-(2,4-dichlorophenoxy)-1-propanol methanesulfonate (ester); bp. 130° C. at 2×10-4 mm. pressure (intermediate 101).

Workup

  1. customexothermic reaction
  2. temperaturethe temperature roses to reflux temperature)
  3. temperatureWhile cooling in a water-bath
  4. additionThe reaction mixture was poured onto water
  5. extractionthe product was extracted with 2,2'-oxybispropane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. distillationThe residue was distilled by vacuum distillation

Sources & evidence

ORD record
ord-70763a5f94f747b0b6c0fd658e27c2b0
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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