Chlorosulfonic acid → Ethyl 2-(4-(chlorosulfonyl)-2-ethylphenoxy)acetate

HRID 270147

Reaction equation

HRID 270147 reaction equation
[CH2:1]([C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[Cl:16][S:17](O)(=[O:19])=[O:18]>>[Cl:16][S:17]([C:14]1[CH:13]=[CH:12][C:4]([O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:3]([CH2:1][CH3:2])[CH:15]=1)(=[O:19])=[O:18]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 21986411Ethyl (2-ethylphenoxy)acetate

Product 1

HCID 21986343Ethyl 2-(4-(chlorosulfonyl)-2-ethylphenoxy)acetateYield 70%

Conditions

Temperature
0 °C

Procedure

To a 250ml round-bottom flask containing chlorosulfonic acid (30ml) cooled to 0° C. was added ethyl (2-ethylphenoxy)acetate (7.2g, 34.6mmoles) dropwise. Once the addition was complete the ice-bath was removed and the reaction was allowed to warm to room temperature at which the reaction was stirred for 3hours. The reaction was then slowly added to ice and, once the excess chlorosulfonic acid was quenched, the mixture was diluted with CH2Cl2(200ml). The phases were separated and the aqueous fraction washed with CH2Cl2twice. The combined organic fractions were dried over Na2SO4and filtered and concentrated in vacuo to yield 7.2g (70%) of crude product. The crude product was used with no purification.

Workup

  1. additionOnce the addition
  2. customwas removed
  3. temperatureto warm to room temperature at which the reaction
  4. additionThe reaction was then slowly added to ice
  5. customonce the excess chlorosulfonic acid was quenched
  6. additionthe mixture was diluted with CH2Cl2(200ml)
  7. customThe phases were separated
  8. washthe aqueous fraction washed with CH2Cl2twice
  9. customThe combined organic fractions were dried over Na2SO4and
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f77c5b4fc1248f6a579fbef01fdec08
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Linked notes

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