Water → 4,4-Diphenylbutyl methanesulfonate

HRID 565651Notes

Reaction equation

HRID 565651 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClC(Cl)C.C(N(CC)CC)C>[CH3:19][S:20]([O:11][CH2:10][CH2:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 925194,4-Diphenylbutan-1-ol

Product 1

HCID 138807014,4-Diphenylbutyl methanesulfonateYield 99%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

To an iced-cooled solution of 4,4-diphenyl-1-butanol (5.6 g) in dichloroethane (100 mL), 11 mL of triethylamine and 2.9 mL of methanesulfonyl chloride were added dropwise in the order mentioned. After 30 minutes of stirring, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl, dried over MgSO4, and concentrated to provide 7.5 g of the title compound. Yield 99%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9ddfde998e143e8bc06e50cd97540c8
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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