Hydrochloric Acid → HCID 66685052, compound

HRID 71238Notes

Reaction equation

HRID 71238 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2(/[CH:15]=[CH:16]/[C:17]([O:19]CC)=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([C:9]2(/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86688201(E)-ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)acrylate

Product 1

HCID 66685052HCID 66685052, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)acrylate (Preparation 5C, 53 mg, 0.180 mmol) in MeOH (1 mL) was added 1M NaOH (0.216 mL, 0.216 mmol), and the mixture was stirred at room temperature overnight. The mixture was acidified by the addition of 0.3 mL of 1N HCl, and the product was extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and evaporated to give the (E)-3-(1-(3,4-difluorophenyl)cyclohexyl)acrylic acid as an oil. 1H NMR (400 MHz, CCl3D) δ ppm 11.94 (1H, br. s.), 7.11 (2H, m), 7.02 (1H, d, J=15.82 Hz), 6.98-7.06 (1H, m), 5.62 (1H, d, J=15.82 Hz), 1.83-2.06 (4H, m), 1.37-1.65 (6H, m).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-31fa2d19acc546c9b692c0c8b77c5289
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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