Hydrochloric Acid → HCID 66685052, compound

HRID 714245Notes

Reaction equation

HRID 714245 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 Int. 3-C, 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, CDCl3) δ ppm 11.94 (1 H, br. s.), 7.11 (2 H, m), 7.02 (1H, d, J=15.82 Hz), 6.98-7.06 (1H, m), 5.62 (1 H, d, J=15.82 Hz), 1.83-2.06 (4 H, m), 1.37-1.65 (6 H, 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-b7d7f0a566784228a0890d9c2352ee63
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

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