Water → (1-Oxo-2-isopropyl-6,7-dichloroinden-5-yloxy)acetic acid

HRID 1283878Notes

Reaction equation

HRID 1283878 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(Br)[CH:18]([CH3:20])[CH3:19].N12CCCC1=NCCC2.O>CS(C)=O>[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:3]1[CH:18]([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 21516801(1-Oxo-2-bromo-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid

Product 1

HCID 21516803(1-Oxo-2-isopropyl-6,7-dichloroinden-5-yloxy)acetic acidYield 69.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(1-Oxo-2-bromo-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid (17.3 g., 0.044 mole) is dissolved in dimethyl sulfoxide (DMSO, 100 ml.) stirred under nitrogen and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (13 g.) is added dropwise. When the exothermic reaction ceases, the mixture is stored at 20°-25°C. for 1 1/2 hours and then poured into water (1.5 l.). The precipitate is recrystallized from acetic acid-water (1:1) to afford (1-oxo-2-isopropyl-6,7-dichloroinden-5-yloxy)acetic acid (9.6 g.), m.p. 175.5°-176°C.

Workup

  1. customWhen the exothermic reaction ceases
  2. customis stored at 20°-25°C. for 1 1/2 hours
  3. customThe precipitate is recrystallized from acetic acid-water (1:1)

Sources & evidence

ORD record
ord-ea8213be8f704e768a8a70703ae43dc3
Source dataset
uspto-grants-1976_08
Patent number
US03976686

Reaction notes

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