2-[3-(2-Carboxycyclohexylmethyloxy)phenyl]propionic acid → 2-(6,6a,7,8,9,10,10a,11-Octahydro-11-oxodibenz[b,e]oxepin-3-yl)propionic acid

HRID 223714Notes

Reaction equation

[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=1)([OH:3])=O>O>[O:3]=[C:1]1[CH:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]2[CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])[CH:15]=[CH:16][C:17]1=2

Participants

Conditions

Temperature: 100 °C

Procedure

2-[3-(2-Carboxycyclohexylmethyloxy)phenyl]propionic acid (14 g) was added to polyphophoric acid (80 g) and the mixture was heated with stirring for 2.5 hours in an oil bath maintained at 100° C. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layers were washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel, using methanol-chloroform (2:98, v/v) as an eluent, to give 2-(6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenz[b,e]oxepin-3-yl)propionic acid (1.05 g) as an oil. IR νmaxfilm cm-1 : 1700, 1680 (C=O). HRMS m/e: 288.1390 (M+) (Molecular weight calculated for C17H20O4 : 288.1362).

Workup

temperaturethe mixture was heated
extractionextracted with ethyl acetate
washThe ethyl acetate layers were washed with water
dry with materialdried over anhydrous sodium sulfate
customevaporated to dryness under reduced pressure
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-a1e43198f3d9409c922b6bfdc2cb541a
Source dataset: uspto-grants-1982_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04356186

Reaction notes

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