Water → (2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoic acid

HRID 229132Notes

Reaction equation

HRID 229132 reaction equation
[C:1]1(=[C:7]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18]C(C)(C)C)=[O:17])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.O>C(Cl)Cl>[C:1]1(=[C:7]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 689777101,1-Dimethylethyl(2E)-3-{4-[cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoate

Product 1

HCID 11267632(2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoic acidYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1,1-dimethylethyl (2E)-3-{4-[cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoate (7) (0.24 g, 0.61 mmol) in CH2Cl2 (6 mL) was cooled in an ice-water bath and stirred under a nitrogen atmosphere. To the cold solution was slowly added trifluoroacetic acid (6 mL). The reaction mixture was stirred in the ice-water bath under a nitrogen atmosphere for 1 h. The reaction mixture was concentrated to give the crude product as a solid. The crude product was dissolved in CH2Cl2 and the solution was concentrated to give a solid. The crude product was transferred to a separatory funnel with the aid of CH2Cl2 and H2O. The organic phase was removed and the aqueous phase that contained suspended solids was extracted twice with CH2Cl2. The organic phase was removed and the aqueous suspension was filtered with the aid of H2O. The filtered white solid was dissolved in CH2Cl2 and MeOH and the solution was filtered. The filtrate was concentrated and the resulting solid was dried in a vacuum oven to give 135 mg (67%) of compound 8 as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.52 (m, 6H), 2.15 (m, 4H), 6.44 (d, J=15.9 Hz, 1H), 6.66 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 7.05 (d, J=8.0 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.57 (d, J=8.0 Hz, 2H), 9.31 (s, 1H), 12.31 (br s, 1H). The sample was silated prior to EI analysis. HRMS (EI) Calcd for C28H38O3Si2: 478.2360 (M+.). Found: 478.2376.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give the crude product as a solid
  3. concentrationthe solution was concentrated
  4. customto give a solid
  5. customThe organic phase was removed
  6. extractionwas extracted twice with CH2Cl2
  7. customThe organic phase was removed
  8. filtrationthe aqueous suspension was filtered with the aid of H2O
  9. dissolutionThe filtered white solid was dissolved in CH2Cl2
  10. filtrationMeOH and the solution was filtered
  11. concentrationThe filtrate was concentrated
  12. customthe resulting solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-c8e0a8ddf4b9403f9453526e59626b9f
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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