2-Cyclopentyl-1-(2,3-dichloro-4-methoxyphenyl)prop-2-en-1-one → 6,7-Dichloro-2-cyclopentyl-5-methoxy-2,3-dihydroinden-1-one

HRID 596994Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

2',3'-Dichloro-4'-methoxy-2-cyclopentylacrylophenone (33.3 g.) is dissolved in 98° sulfuric acid (150 ml.) and stirred at 20° C. for 1.5 hours. The solution then is added dropwise with stirring to ice water. The aqueous phase is decanted from the gummy product and fresh water is added. After 20 hours the gum solidifies and is crystallized from hexane-benzene (3:1) to obtain 2-cyclopentyl-5-methoxy-6,7-dichloro-1-indanone, m.p. 116°-117° C.

Workup

additionThe solution then is added dropwise
customThe aqueous phase is decanted from the gummy product and fresh water
additionis added
waitAfter 20 hours the gum solidifies
customis crystallized from hexane-benzene (3:1)

Sources & evidence

ORD record: ord-cd4edc50a0a544f0a82daeb0d178fe39
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04012524

Reaction notes

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