Water → Glycidyl tosylate

HRID 1739457Notes

Reaction equation

HRID 1739457 reaction equation
Cl[CH2:2][CH:3]([OH:6])[CH2:4][OH:5].O.[OH-].[Na+].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)([O:5][CH2:4][CH:3]1[O:6][CH2:2]1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 72903-Chloro-1,2-propanediolHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 160868Glycidyl tosylateYield 68.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 10 g of 3-chloro-1,2-propanediol (0.09 mol) and 40 ml of water, was added dropwise at 24-26° C. 16.6 g of 24% sodium hydroxide (0.1 mol). The solution was stirred for one hour. The solution was cooled and thereto 0.17 g of N,N-dimethylaminopyridine (0.0014 mol) and 17.2 g of p-toluenesulfonyl chloride (0.09 mol) in 50 ml of toluene, and then 16.6 g of 24% sodium hydroxide (0.1 mol) were added under stirring at 0-5° C. And the solution was stirred for one hour. After separation with a separating funnel, the organic layer was washed with 50 ml of 1% hydrochloric acid and 50 ml of water. The excess solvent was removed under vacuo. The chemical purity by HPLC at that time was 98.3%. The residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V) to give 14.0 g of glycidyl tosylate. Chemical purity: 99.6% (yield: 68%)

Workup

  1. temperatureThe solution was cooled
  2. stirringunder stirring at 0-5° C
  3. stirringAnd the solution was stirred for one hour
  4. customAfter separation with a separating funnel
  5. washthe organic layer was washed with 50 ml of 1% hydrochloric acid and 50 ml of water
  6. customThe excess solvent was removed under vacuo
  7. customThe residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V)

Sources & evidence

ORD record
ord-43a31abf977e47c2a2292dc27165bb22
Source dataset
uspto-grants-1999_10
Patent number
US05965753

Reaction notes

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