Water → (1-Phenylcyclopentyl)methyl methanesulfonate

HRID 1788637Notes

Reaction equation

HRID 1788637 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:6][CH2:7][C:8]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][CH2:10][CH2:11][CH2:12]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 123544(1-Phenylcyclopentyl)methanol

Product 1

HCID 19437914(1-Phenylcyclopentyl)methyl methanesulfonateYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonyl chloride (1.62 g) in dry dichloromethane (10 ml) was added over 20 minutes to a stirred mixture of 1-hydroxymethyl-1-phenylcyclopentane (1.91 g) and triethylamine (1.64 g) in dry dichloromethane (50 ml) at 0° C. (white precipitate). After 1 hour, all at about 0° C., water was added to the reaction mixture and the organic and aqueous layers were separated. The organic layer was washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate and water, then dried over magnesium sulphate and concentrated to give almost pure 1-methanesulphonyloxymethyl-1-phenylcyclopentane (2.85 g) as an almost colourless oil which crystallised completely on standing in the fridge, melting point 55°-60° C., 1H n.m.r. (CDCl3): δ 2.51 (3H, s, CH3SO2), 4.16 (2H, s, CH2OSO2CH3).

Workup

  1. customthe organic and aqueous layers were separated
  2. washThe organic layer was washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate and water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cc8d76d9bbd3464eaacc9e16c95fb543
Source dataset
uspto-grants-1987_08
Patent number
US04684396

Reaction notes

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