3,4,5-Trimethoxyhydrocinnamic acid → 5,6,7-Trimethoxy-1-indanone

HRID 1977998

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-(3,4,5-trimethoxyphenyl)propionic acid (9.40 g, 39.1 mmol) and polyphosphoric acid (50 g) was stirred for 2 hours at 80° C. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from ethyl acetate/isopropyl ether to give 7.71 g (yield 89%) of the above-titled compound, m.p. 114-115° C.

Workup

extractionwas subjected to extraction with ethyl acetate
washThe extract solution was washed with brine, which
dry with materialwas dried over anhydrous magnesium sulfate
distillationby distilling off the solvent under reduced pressure
customThe residue was recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record: ord-be88cccdd0e04b61a3c603911ae5807d
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235789B1

Linked notes

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