Sodium Hydroxide → 1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid

HRID 1596802Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19]CC)=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Crude ethyl 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylat (30 g) is dissolved in EtOH (96%, 150 ml) and aqueous 2N NaOH (150 ml). The solution is refluxed for 1 hour. ½ of the volume is removed in vacuo. The aqueous phase is extracted with EtOAc (2×100 ml). The aqueous phase is made acidic (pH=1, conc. HCl) and after cooling to 5° C. the white crystals are filtered off. Yield 16 g. Overall yield is 66% starting from 5-ethoxycarbonylphthalide. Mp 187-190° C.

Workup

temperatureThe solution is refluxed for 1 hour
custom½ of the volume is removed in vacuo
extractionThe aqueous phase is extracted with EtOAc (2×100 ml)
filtrationare filtered off

Sources & evidence

ORD record: ord-972e933fb03a43018afe59087d33f334
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291689B1

Reaction notes

Loading…