Hydrochloric Acid → 5-Acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoic acid

HRID 1849732Notes

Reaction equation

HRID 1849732 reaction equation
[C:1]([C:4]1[C:5]([O:15][CH2:16][C:17]23[CH2:26][CH:21]4[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]4)[CH2:18]2)[CH2:24]3)=[CH:6][C:7]([F:14])=[C:8]([CH:13]=1)[C:9]([O:11]C)=[O:10])(=[O:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([C:4]1[C:5]([O:15][CH2:16][C:17]23[CH2:26][CH:21]4[CH2:20][CH:19]([CH2:25][CH:23]([CH2:22]4)[CH2:24]2)[CH2:18]3)=[CH:6][C:7]([F:14])=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86703608Methyl 5-acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoate

Product 1

HCID 867036095-Acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoate (0.75 g, 2.10 mmol) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.441 g, 10.50 mmol) in water (4 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 hours. After adjusting the reaction mixture to pH 2 with 1 N hydrochloric acid, the mixture was extracted with ethyl acetate (3×20 mL). The combined organic phase was washed with brine (5 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo yielded the title compound as a colorless oil (0.727 g, quant.), which was used without further purification: MS (ES−) m/z 345.3 (M−1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  2. washThe combined organic phase was washed with brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2c23ac96afe146388b1f07914dd0d9cf
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…