Water → 3-Methoxypropyl 4-methylbenzenesulfonate

HRID 1809806Notes

Reaction equation

HRID 1809806 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].O>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 741163-Methoxy-1-propanol

Product 1

HCID 135229883-Methoxypropyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methoxy-1-propanol (6 g, 65.24 mmol), triethylamine (27.5 mL, 195.7 mmol) and tosylchloride (18.85 g, 97.9 mmol) in methylene chloride (50 mL) is stirred for 3 h at room temperature under nitrogen. The mixture is poured into H2O, and the aqueous layer extracted twice with methylene chloride. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica gel (hexane/EtOAc 4/1) to afford the title compound as an orange oil: MS 261.9 [M+18]; Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 5.21 min.

Workup

  1. extractionthe aqueous layer extracted twice with methylene chloride
  2. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash column chromatography on silica gel (hexane/EtOAc 4/1)

Sources & evidence

ORD record
ord-3593a0dbe66d467eb0bdb20e43bb9333
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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