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

HRID 1943556
Notes
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Reaction equation

HRID 1943556 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66682456Ethyl 4-ethoxy-2,3-difluoro-4'-biphenylbenzoate

Product 1

HCID 670823704-Ethoxy-2,3-difluoro-4'-biphenylbenzoic acidYield 48.2%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

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

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. additionmixed
  4. customhad separated into two phases of organic and
  5. extractionaqueous phases, and extraction into an organic phase
  6. customThe organic phase obtained
  7. washwashed sequentially with water
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes