[(6,7-Dichloro-2-cyclopentyl-2-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]acetic acid → (1-Oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetyl chloride

HRID 2083490Notes

Reaction equation

HRID 2083490 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15](O)=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH3:18].S(Cl)([Cl:26])=O>C1C=CC=CC=1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:13][CH2:14][C:15]([Cl:26])=[O:16])=[C:8]([Cl:12])[C:9]=2[Cl:11])[CH2:4][C:3]1([CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1)[CH3:18]

Participants

4

Reactant 2

HCID 3667[(6,7-Dichloro-2-cyclopentyl-2-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 20193603(1-Oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid (3.57 g., 0.01 mole) and thionyl chloride (2.38 g., 0.02 mole) in benzene (50 ml.) is refluxed for 1 hour. The excess thionyl chloride and benzene are evaporated at reduced pressure as is a subsequent 50 ml. portion of benzene affording (1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetyl chloride as a yellow oil which is used in step B without further purification.

Workup

  1. customThe excess thionyl chloride and benzene are evaporated at reduced pressure

Sources & evidence

ORD record
ord-a1e0a696d238491d9ab3a062fc55bf15
Source dataset
uspto-grants-1978_04
Patent number
US04085219

Reaction notes

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