Hydrochloric Acid → HCID 86733640, compound

HRID 1283871Notes

Reaction equation

HRID 1283871 reaction equation
[CH3:1][C:2]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[C:15]1([C:23](Cl)=[O:24])([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[O:21]=[C:20]1[C:11]2[C:12](=[C:13]([Cl:14])[C:2]([CH3:1])=[C:3]([O:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH:10]=2)[C:23](=[O:24])[C:15]21[CH2:19][CH2:18][CH2:17][CH2:16]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 15618605Cyclopentane-1,1-dicarbonyl dichlorideHCID 54506780HCID 54506780, compound

Product 1

HCID 86733640HCID 86733640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A stirred solution of methyl (2-methyl-3-chlorophenoxy)acetate (3.7 g., 0.0172 mole) and cyclopentane-1,1-dicarbonyl chloride (3.5 g., 0.018 mole) in methylene chloride (200 ml.) is cooled to 0°C. and treated with aluminum chloride (7.2 g., 0.054 mole) in several portions during a 15 minute period. The reaction is stirred at 25°C. for 18 hours than at reflux for 5 hours, cooled and poured into 1N-hydrochloric acid. Evaporation of the methylene chloride at reduced pressure affords methyl [1',3'-dioxo-4'-chloro-5'-methyl-spiro(cyclopentane-1,2'-indan)-6'-yloxy]acetate which melts at 152°-153.5°C. after recrystallization from ethanol-water.

Workup

  1. temperatureat reflux for 5 hours
  2. temperaturecooled
  3. customEvaporation of the methylene chloride at reduced pressure

Sources & evidence

ORD record
ord-f3ebc54026a34f99bb8ee751d5045d36
Source dataset
uspto-grants-1976_08
Patent number
US03976681

Reaction notes

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