Water → HCID 20373898, compound

HRID 1834692Notes

Reaction equation

HRID 1834692 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])[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]1[CH2:24][CH3:25].S(Cl)([Cl:29])(=O)=O.O>C(O)(=O)C>[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])[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:3]1([CH2:24][CH3:25])[Cl:29]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 12395614HCID 12395614, compound

Product 1

HCID 20373898HCID 20373898, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(1-Oxo-2-ethyl-3-phenyl-6,7-dichloro-5-indanyloxy)acetic acid (5.6 g., 0.0143 mole) is dissolved in warm acetic acid (70 ml.) and treated with sulfuryl chloride (1.3 ml., 0.016 mole). The solution is heated on a steam bath for two hours, cooled to room temperature and then added slowly to cold water (500 ml.) with stirring. The product precipitates and is collected by suction filtration, washed well with water and air-dried overnight to afford 5.9 g. of crude product. The crude product is recrystallized several times from ethanol (30 ml.) and water (20 ml.) and then from nitromethane to afford substantially pure (1-oxo-2-ethyl-3-phenyl-2,6,7-trichloro-5-indanyloxy)acetic acid, m.p. 190°-192° C.

Workup

  1. temperatureThe solution is heated on a steam bath for two hours
  2. customThe product precipitates
  3. filtrationis collected by suction filtration
  4. washwashed well with water
  5. customair-dried overnight
  6. customto afford 5.9 g
  7. customThe crude product is recrystallized several times from ethanol (30 ml.) and water (20 ml.)

Sources & evidence

ORD record
ord-1a62b7e0054a41c083bfc11af890e621
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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