2-Chloroethanol → 2-Chloroethyl Benzenesulfonate

HRID 1063819Notes

Reaction equation

HRID 1063819 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].[C:5]1([S:11](Cl)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1>O>[Cl:1][CH2:2][CH2:3][O:4][S:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 1049PyridineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 136344852-Chloroethyl BenzenesulfonateYield 0.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloroethanol (1168 g, 975 mol) and benzene sulfonyl chloride (2780 g, 2015 mol) were stirred together at −5° C. and pyridine (2158 g, 2200 mol) was added over a 3 hours period, maintaining the temperature below 0° C. The reaction was stirred for a further 3 hours at −5° C. to 0° C. and was then allowed to warm to room temperature over 18 hours. After pouring into a mixture of ice (10 liters) and water (10 liters) the reaction was stirred for 15 minutes, extracted with ether (10 liters) and the organic phase was washed with 5N HCl (2×2 liters) and water (2×4 liters). It was then dried over MgSO4 and concentrated under reduced pressure to give benzene sulfonic acid 2-chloro-ethyl ester (1921 g) as an orange oil. 1H NMR (250 MHz, CDCl3): δ=7.78-8.02 (2H, m), 7.58-7.78 (3H, m), 420-4.45 (2H, t), 3.60-3.81 (2H, t) ppm.

Workup

  1. temperaturemaintaining the temperature below 0° C
  2. stirringwas stirred for 15 minutes
  3. extractionextracted with ether (10 liters)
  4. washthe organic phase was washed with 5N HCl (2×2 liters) and water (2×4 liters)
  5. dry with materialIt was then dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-afca6076ec794bbda5f513c9c1fa9b41
Source dataset
uspto-grants-2005_11
Patent number
US06967204B2

Reaction notes

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