Triethylamine → 6-Phenylhex-1-yl methylsulfonate

HRID 1703104Notes

Reaction equation

HRID 1703104 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-8858bfde2c0d4132bcecb9ac31a9c0a0
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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