Hydrochloric Acid → Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)

HRID 1732281Notes

Reaction equation

HRID 1732281 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl>N1C=CC=CC=1>[S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH3:16])=[CH:7][CH:8]=1)([O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 80192-Methoxyethanol

Product 1

HCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)Yield 86.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 38 g of 2-methoxyethanol in 12 ml of pyridine was added portionwise, over two hours, 95.3 g of p-toluenesulfonyl chloride at 0° C. The reaction mixture was stirred for 20 hours, poured into 200 ml of concentrated hydrochloric acid and 1 liter of ice cubes, extracted with methylene chloride and washed successively with methylene chloride, water and a saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and stripped to yield 99 g of 2-methoxyethyl tosylate as a yellow oil.

Workup

  1. customat 0° C
  2. extractionextracted with methylene chloride
  3. washwashed successively with methylene chloride, water
  4. dry with materialThe organic phase was dried over magnesium sulfate

Sources & evidence

ORD record
ord-a9425bb64ae844edb4784aadb6371b99
Source dataset
uspto-grants-1980_12
Patent number
US04237123

Reaction notes

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