Pyridine → Methanesulfonate

HRID 980220Notes

Reaction equation

HRID 980220 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[CH2:15][CH3:16])=[CH:10][CH:9]=1.N1C=CC=CC=1>ClCCl>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][OH:3])=[CH:10][CH:9]=1.[CH3:1][S:2]([O-:4])(=[O:7])=[O:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 92218Benzenemethanol, .alpha.-ethyl-4-methoxy-

Product 2

HCID 794063-(4-Methoxyphenyl)-1-propanolHCID 85257MethanesulfonateYield 421.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl sulphonyl chloride (12.5 g, 0.11M) was added dropwise to a stirred solution of p-methoxyphenylpropanol (16.6 g, 0.10M) in dichloromethane (60 ml)/pyridine (20 ml) at 0° C. The reaction mixture was maintained at 0° C. for 12 hours, then diluted with dichloromethane (250 ml) and washed with hydrochlorid acid (5×50 ml of 5M.1-1). The solution was washed with water, dried (MgS04) and the solvent was evaporated off under reduced pressure to give 3-(4-methoxyphenyl)propan-1-ol, methane sulphonate (20 g), as a colourless crystalline solid, m.p. 41-42° C. (pentane).

Workup

  1. washwashed with hydrochlorid acid (5×50 ml of 5M.1-1)
  2. washThe solution was washed with water
  3. customdried (MgS04)
  4. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-6c1ed3ff96d344dabadb5b5bd68ecafc
Source dataset
uspto-grants-1987_01
Patent number
US04636518

Reaction notes

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