Sodium Hydroxide → 3,3-Bis(3-fluorophenyl)propionic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:9][C:10]([O:12]CC)=[O:11])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 3,3-bis(3-fluorophenyl)propionate (39.08 g, 134.8 mmol) in absolute ethanol (500 mL) was treated with 5N NaOH (500 mL) and stirred at ambient temperature for 16 hr. After this time the reaction mixture was concentrated (removal of ethanol) on a rotary evaporator and diluted with water (1 L). The aqueous mixture was washed once with diethyl ether (500 mL) and the remaining aqueous mixture acidified (pH˜1) by the addition of concentrated HCl. The aqueous phase was extracted with methylene chloride (4×250 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated to afford 31.76 g (90%) of the title compound as a white solid. GC/EI-MS analysis gave a single component: Rt=6.60 min, m/z (rel. int.) 262 (M+, 13), 243 (1), 216 (40), 203 (85), 201 (54), 183 (100), 170 (11), 121 (31), 101 (43), 96 (24), and 75 (45).