Sulfuric Acid → {[6,7-Dichloro-1-oxo-2-(propan-2-yl)-2,3-dihydro-1H-inden-5-yl]oxy}acetic acid

HRID 1834687Notes

Reaction equation

[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:20])[C:15](=[CH2:19])[CH:16]([CH3:18])[CH3:17])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].S(=O)(=O)(O)O>O>[O:20]=[C:14]1[C:11]2[C:10](=[CH:9][C:3]([O:4][CH2:5][C:6]([OH:8])=[O:7])=[C:2]([Cl:1])[C:12]=2[Cl:13])[CH2:19][CH:15]1[CH:16]([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

2,3-Dichloro-4-(2-methyleneisovaleryl)phenoxyacetic acid (8.8 g., 0.0278 mole) is added to concentrated sulfuric acid (50 ml.). The mixture is stirred and heated at 60° C. for two hours and then at 80° C. for three hours. The dark solution is cooled and added dropwise with stirring to water (1 l.). A pale yellow gum separates and after 16 hours at 20°-25° C. changes to a cream colored powder (8.6 g., m.p. 161°-164° C.) which is recrystallized from acetic acid-water (1:1) to afford 6.9 g. of (1-oxo-2-isopropyl-7,8-dichloro-5-indanyloxy)acetic acid, m.p. 166°-167.5° C.

Workup

temperatureThe dark solution is cooled
additionadded dropwise
waitA pale yellow gum separates and after 16 hours at 20°-25° C. changes to a cream colored
custompowder (8.6 g., m.p. 161°-164° C.) which is recrystallized from acetic acid-water (1:1)
customto afford 6.9 g

Sources & evidence

ORD record: ord-a8e0a9bff3124f258a888379acc61d45
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04070539

Reaction notes

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