Water → 3-Methoxypropyl 4-methylbenzenesulfonate

HRID 2354963Notes

Reaction equation

HRID 2354963 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-906e4f55ecff4f838c68b95c7e87ac54
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

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