Acetic Acid → HCID 15296555, compound

HRID 2210091Notes

Reaction equation

[C:1]([CH2:3][CH2:4][O:5][C:6]1[C:7]([CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)#N.P(=O)(O)(O)[OH:23].C(O)(=O)C.C(OCC)(=O)C>O>[OH:12][C:8]1[CH:9]=[CH:10][C:11]2[C:1](=[O:23])[CH2:3][CH2:4][O:5][C:6]=2[C:7]=1[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 3.5 g (12.5 mmol) of 3-(2-cyanoethoxy)-2-(3-phenylpropyl)phenol (preceding example), 16 mL of 85% phosphoric acid, and 7.7 mL of acetic acid was stirred and heated at 125° C. for 23 hr. After being cooled, the mixture was diluted with water and worked-up with ethyl acetate in the usual manner giving 4 g of a red oil. This material was chromatographed on silica gel. Elution with hexane-ethyl acetate mixtures afforded 2.3 g (65.2%) of the title compound as a yellow solid.

Workup

temperatureAfter being cooled

Sources & evidence

ORD record: ord-61db1e40ff5447f6a0174fb40834222e
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457124

Reaction notes

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