Sodium Hydroxide → 3,3-Bis(3-fluorophenyl)propionic acid

HRID 1167249Notes

Reaction equation

HRID 1167249 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22996571Ethyl 3,3-bis(3-fluorophenyl)propionate

Product 1

HCID 220157633,3-Bis(3-fluorophenyl)propionic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. concentrationAfter this time the reaction mixture was concentrated
  2. custom(removal of ethanol)
  3. customon a rotary evaporator
  4. additiondiluted with water (1 L)
  5. washThe aqueous mixture was washed once with diethyl ether (500 mL)
  6. additionby the addition of concentrated HCl
  7. extractionThe aqueous phase was extracted with methylene chloride (4×250 mL)
  8. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e839d45632124f9886ddc7c91e259530
Source dataset
uspto-grants-2003_09
Patent number
US06617358B1

Reaction notes

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