Triethylamine → 6-Phenylhex-1-yl methylsulfonate

HRID 2052509Notes

Reaction equation

HRID 2052509 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5201106-Phenyl-1-hexanol

Product 1

HCID 130797026-Phenylhex-1-yl methylsulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-4 °C

Procedure

To a chilled (-4° C.) solution of 19.4 g. of 6-phenylhexanol (prepared as described in Example 46) and 15.1 g. of triethylamine in 500 ml. of dichloromethane is added dropwise, over 5 minutes, 12.6 g. of methanesulfonyl chloride. The mixture is stirred at -10° C. for 30 minutes and the solution washed successively with 200 ml. of cold water, 200 ml. of cold 10% hydrochloric acid, 200 ml. of cold saturated sodium bicarbonate and 200 ml. of cold saturated sodium chloride solution. The organic layer is dried over magnesium sulfate and the solvent removed under reduced pressure to give 6-phenylhexanol O-methanesulfonate as an oil.

Workup

  1. washthe solution washed successively with 200 ml
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-585aae70521b4cb4855d1b1c8fe164ea
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

Loading…