Hydrochloric Acid → 3-(1-(3,4-Difluorophenyl)cyclohexyl)propanoic acid

HRID 714244Notes

Reaction equation

HRID 714244 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][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([CH2:15][CH2:16][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 Hydroxide2×HCID 66685623Ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)propanoate

Product 1

HCID 666850543-(1-(3,4-Difluorophenyl)cyclohexyl)propanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)propanoate (Int. 3-D, 540 mg, 1.822 mmol) in MeOH (15 mL) was added 1N NaOH (3.64 mL, 3.64 mmol), and the mixture was stirred at room temperature for 20 hrs. Since the reaction was not complete on TLC, an additional 1.82 mL of 1N NaOH was added, and it was continued to stir for 3 hrs. TLC showed that the reaction was complete. Next, the reaction mixture was acidified with the addition of 6 mL of 1N HCl, and the product was extracted with EtOAc. The extract was washed with water and brine, dried over Na2SO4, and evaporated to give 3-(1-(3,4-difluorophenyl)cyclohexyl)propanoic acid (Int. 3, 489 mg, 1.822 mmol, 100% yield) as a white solid.

Workup

  1. stirringto stir for 3 hrs
  2. extractionthe product was extracted with EtOAc
  3. washThe extract was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b0af7df9ab4947578cbd6a435ff11fe2
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

Loading…