Propylene Glycol → 1-(Tosyloxy)-2-propanol

HRID 1017268Notes

Reaction equation

HRID 1017268 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:16])[CH:13]([OH:15])[CH3:14].C(N(CC)CC)C>ClCCl.C(OCC)C.CNC>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:16][CH2:12][CH:13]([OH:15])[CH3:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 1030Propylene GlycolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 109988101-(Tosyloxy)-2-propanolYield 97%

Reagents, catalysts & solvents 3

HCID 674DimethylamineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulphonyl chloride (19.4 g, 102 mmol) was added to a stirred solution of propane-1,2-diol (30 ml), triethylamine (15 ml, 106 mmol), N,N-dimethylamine (108 mg, 0.87 mmol) in dichloromethane (100 ml) at +5° C. The mixture was stirred for 2 hours at +5° C. and overnight at room temperature then diluted with diethyl ether (300 ml) and washed 2M aqueous hydrochloric acid, water (twice) and brine. The combined organic extracts were dried (Na2SO4) and concentrated to give the title compound (22.8 g, 97%).

Workup

  1. washwashed 2M aqueous hydrochloric acid, water (twice) and brine
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8f2f48c2f27844098076a2f6faab37c4
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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