Hydrochloric Acid → (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid

HRID 2380642Notes

Reaction equation

[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)/[CH:4]=[CH:5]/[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 60 °C

Procedure

A toluene (8 ml) solution of the above ester (2.38 g, 6.7 mmol) was added to powdery sodium hydroxide (0.34 g, 8.5 mmol) under argon atmosphere, and the whole was stirred at 60° C. for 5 hours. The reaction mixture was neutralized with 1M hydrochloric acid (10 ml) and extracted with ethyl acetate (25 ml×3 times). The organic layer was washed with water, saturated sodium chloride aq solution and then dried over anhydrous magnesium sulfate. Concentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1) gave 1.70 g (78% yield) of (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid. mp=225°-230° C. Rf =0.52 (hexane:ethyl acetate=1:1) IR (KBr): 3350, 2400, 3025, 1690, 1615, 1515, 1430, 1320, 1225, 1165, 1100, 1080, 1005, 965, 860, 850, 595, 580 cm-1.

Workup

extractionextracted with ethyl acetate (25 ml×3 times)
washThe organic layer was washed with water, saturated sodium chloride aq solution
dry with materialdried over anhydrous magnesium sulfate
customConcentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-5b5687f8450141daa202ed89c2bd0268
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05369109

Reaction notes

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