Hydrochloric Acid → 4-Ethoxy-2,3-difluoro-4'-biphenylbenzoic acid

HRID 1943556Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[C:6]([F:27])[C:5]=1[F:28])[CH3:2].[OH-].[Na+].O.Cl>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]3[C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][CH:15]=2)=[C:6]([F:27])[C:5]=1[F:28])[CH3:2]

Participants

Conditions

Temperature: 30 °C

Procedure

The compounds (3) (29.1 g), sodium hydroxide (11.4 g), Solmix A-11 (100 ml) and water (100 ml) were mixed, and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled to 30° C., and then aqueous 6N-hydrochloric acid solution (100 ml) and toluene (200 ml) were added hereto and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed sequentially with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate, giving 13.0 g of 4-ethoxy-2,3-difluoro-4′-biphenylbenzoic acid (44). The yield based on the compound (3) was 49.2%.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 2 hours
additionmixed
customhad separated into two phases of organic and
extractionaqueous phases, and extraction into an organic phase
customThe organic phase obtained
washwashed sequentially with water
dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-5480e426a06b488cae572174ad93f673
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394294B2

Reaction notes

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