Chlorosulfonic acid → [1-Oxo-2-(4-chlorosulfonylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

HRID 839698Notes

Reaction equation

HRID 839698 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl:25][S:26](O)(=[O:28])=[O:27]>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([C:18]1[CH:23]=[CH:22][C:21]([S:26]([Cl:25])(=[O:28])=[O:27])=[CH:20][CH:19]=1)[CH3:24]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 42266Indacrinone

Product 1

HCID 12423626[1-Oxo-2-(4-chlorosulfonylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

Conditions

Temperature
0 °C

Procedure

(1-Oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetic acid (0.50 g., 0.0014 mole) is added portionwise with stirring to chlorosulfonic acid (5 ml.) in an ice-water bath. The reaction mixture is stirred at 0° C. for 2 hours, left to come to ambient temperature for 2 hours, then slowly added to crushed ice to precipitate 0.51 g. of [1-oxo-2-(b 4-chlorosulfonylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 209°-210° C. after crystallization from acetic acid:water, 3:2.

Workup

  1. waitleft
  2. waitto come to ambient temperature for 2 hours
  3. additionslowly added
  4. customto crushed ice
  5. customto precipitate 0.51 g
  6. customof [1-oxo-2-(b 4-chlorosulfonylphenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 209°-210° C. after crystallization from acetic acid

Sources & evidence

ORD record
ord-cfd7c9db1d184604950d9def6887e343
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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