Phosphorus oxychloride → Ethyl (chlorosulfonyl)acetate

HRID 1721389

Reaction equation

HRID 1721389 reaction equation
[S:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(O)(=[O:3])=[O:2].O=P(Cl)(Cl)[Cl:13]>>[Cl:13][S:1]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])=[O:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12216623Ethyl sulfoacetate

Product 1

HCID 12225100Ethyl (chlorosulfonyl)acetate

Conditions

Temperature
125 °C

Procedure

1H NMR (CDCl3): δ1.35 (t, 3H), 4.1 (s, 2H), 4.25 (q, 2H). A mixture of ethyl sulfoacetate (16.82 g, 100 mM) and POCl3 (30.67 g, 200 mM) was heated at 125° C. for 5 hours. The mixture was cooled and filtered, and excess POCl3 was removed to give ethyl chlorosulfonylacetate. The ethyl chlorosulfonylacetate (18.66 g, 100 mM) was added dropwise with stirring to a solution of 2,4,6-triisopropylphenol (22.1 g, 100 mM) in 50 mL CH2Cl2 maintained at 0° C. The mixture was stirred at room temperature for an additional 18 hours. The solvent was removed and the residue was redissolved in 100 mL ethyl acetate and washed with 1 N HCl and brine. The ethyl acetate was evaporated to provide ethyl (2,4,6-triisopropylphenoxysulfonyl)acetate.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customexcess POCl3 was removed

Sources & evidence

ORD record
ord-917051f84c04426783e01bcdb69b05a3
Source dataset
uspto-grants-1996_04
Patent number
US05510379

Linked notes

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