Sodium Hydroxide → 2-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic Acid
Reaction equation
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)=[CH:7][C:6]=1[F:26])C.[OH-].[Na+]>C(O)C.CO.O1CCCC1>[F:26][C:6]1[CH:7]=[C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)[CH:9]=[CH:10][C:5]=1[C:4]([OH:27])=[O:3]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
A solution of 2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid ethyl ester (Compound 9, 0.1 g, 0.274 mmol) in ethanol(4 mL), methanol (2 mL) and tetrahydrofuran (2 mL) was treated with 1M aqueous sodium hydroxide solution and heated at 70° C. for 1 h. The volatiles were distilled off in vacuo and the residue was diluted with water and dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a solid that was recrystallized from hot aqueous acetonitrile to afford the title compound (0.025 g, 27%).
Workup
- distillationThe volatiles were distilled off in vacuo
- additionthe residue was diluted with water and dilute hydrochloric acid
- extractionextracted with ethyl acetate (×2)
- extractionThe combined organic extract
- dry with materialwas dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customto afford a solid
- customthat was recrystallized from hot aqueous acetonitrile
Sources & evidence
- ORD record
- ord-57947630bac04d2fa47f711bc6d7f5cf
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06252090B1
Reaction notes
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