Pyridine → 3-Methoxypropyl 4-methylbenzenesulfonate

HRID 252267Notes

Reaction equation

HRID 252267 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][CH2:16][OH:17].N1C=CC=CC=1>O>[CH3:12][O:13][CH2:14][CH2:15][CH2:16][O:17][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 741163-Methoxy-1-propanol

Product 1

HCID 135229883-Methoxypropyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Methyl-benzenesulfonyl chloride (21 g, 110.0 mmol, 1.1 equiv.) was added at 0° C. to a solution of 3-methoxy-propan-1-ol (9 g, 100.0 mmol, 1.0 equiv.) in pyridine (16.1 ml, 200.0 mmol, 2.0 equiv.). After 1 hr at 0° C. a white solid was formed. It was diluted with water and extracted twice with ethyl acetate. The combined organics were washed with KHSO4/K2SO4 and brine, dried over Na2SO4, filtered, evaporated and crystallized from ether (hygroscopic) to give toluene-4-sulfonic acid 3-methoxy-propyl ester, 21.4 g, m/e 245.0 (MH+).

Workup

  1. customAfter 1 hr at 0° C. a white solid was formed
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organics were washed with KHSO4/K2SO4 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customcrystallized from ether (hygroscopic)

Sources & evidence

ORD record
ord-c144e6287eea4532a469d164592961db
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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