Potassium Carbonate → 2-[3-(2-Carboxycyclohexylmethyloxy)phenyl]propionic acid

HRID 223721Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>CN(C)C=O>[C:13]([CH:3]1[CH2:2][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][O:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)([OH:14])=[O:16]

Participants

Conditions

Temperature: 170 °C

Procedure

To 2-(3-hydroxyphenyl)propionic acid (19.2 g) were added cis-2-(hydroxymethyl)cyclohexanecarboxylic acid lactone (19.5 g), potassium carbonate (19.2 g) and dimethylformamide (200 ml). The mixture was heated with stirring for 3 hours in an oil bath maintained at 170° C. The reaction mixture was treated in substantially the same manner as in Reference Example 2. There was obtained the title compound (14 g) as an oil. IR νmaxfilm cm-1 : 1700 (C=O). MS m/e: 306 (M+).

Workup

temperatureThe mixture was heated
additionThe reaction mixture was treated in substantially the same manner as in Reference Example 2

Sources & evidence

ORD record: ord-63026de869ea45d7b81822ddb8be4a3b
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04356186

Reaction notes

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