Sodium Hydroxide → 4-[Cyclohexylidene(4-hydroxyphenyl)methyl]benzoic acid

HRID 2100137Notes

Reaction equation

HRID 2100137 reaction equation
[C:1]1(=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CCO>[C:1]1(=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68654390Methyl 4-[cyclohexylidene(4-hydroxyphenyl)methyl]benzoate

Product 1

HCID 112205524-[Cyclohexylidene(4-hydroxyphenyl)methyl]benzoic acidYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
87.5 °C

Procedure

To a solution of methyl 4-[cyclohexylidene(4-hydroxyphenyl)methyl]benzoate (156) (0.175 g, 0.54 mmoL) in THF (3 mL) and EtOH (3 mL) was added 1 N NaOH (6 mL) at RT. The reaction mixture was heated between 85-90° C. under a nitrogen atmosphere for 2 h. The oil bath was removed and the reaction mixture was allowed to cool to RT. The reaction mixture was partially concentrated in vacuo to remove the THF and EtOH. The basic aqueous mixture was diluted with H2O and the pH was adjusted to ˜1 (as judged by litmus paper) with 1 N HCl. The acidic aqueous mixture was extracted with CH2Cl2 (2×). The organic extracts were combined, dried (MgSO4), filtered, and the filtrate was concentrated to give the 0.087 g (52%) of compound 157 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.53 (m, 6 H), 2.11 (m, 2 H), 2.17 (m, 2 H), 6.67 (d, J=8.5 Hz, 2 H), 6.85 (d, J=8.5 Hz, 2 H), 7.15 (d, J=8.1 Hz, 2 H), 7.84 (d, J=8.3 Hz, 2 H), 9.35 (s, 1 H), 12.81 (br s, 1). LRMS (ESI): m/z 307 (M−H)−.

Workup

  1. customThe oil bath was removed
  2. temperatureto cool to RT
  3. concentrationThe reaction mixture was partially concentrated in vacuo
  4. customto remove the THF and EtOH
  5. additionThe basic aqueous mixture was diluted with H2O
  6. extractionThe acidic aqueous mixture was extracted with CH2Cl2 (2×)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bbebdb7eaf154cd186602129231e90f7
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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