4-Formylbenzoic acid → 4-[3-(8,8-Dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-oxopropenyl]benzoic acid

HRID 613347Notes

Reaction equation

HRID 613347 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18](=[O:20])[CH3:19])=[CH:15][CH:16]=3)[C:11]([CH3:22])([CH3:21])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[C:23]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)([OH:25])=[O:24].[OH-].[Na+]>CO>[O:20]=[C:18]([C:14]1[CH:15]=[CH:16][C:17]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:9][CH2:10][C:11]([CH3:22])([CH3:21])[C:12]=2[CH:13]=1)[CH:19]=[CH:30][C:29]1[CH:32]=[CH:33][C:26]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 14798Sodium HydroxideHCID 223237763,4-Dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene2×

Product 1

HCID 542966524-[3-(8,8-Dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-oxopropenyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 78.7 mg (0.272 mmol) 3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene (Compound 100G) in 4.0 ml of MeOH was added 53.1 mg (0.354 mmol) of 4-carboxy benzaldehyde, and 80. mg (2.00 mmol; 2.0 ml of 1M aqueous NaOH). The resulting solution was stirred at room temperature for 12 hours, concentrated under reduced pressure, and the residual oil dissolved in EtOAc. The solution was treated with 10% HCl, and the organic layer was washed with H2O, and saturated aqueous NaCl, then dried over Na2SO4. Removal of the solvents under reduced pressure gave the title compound as a colorless solid which was purified by recrystallization from CH3CN. 1H NMR (acetone-d6): δ 8.00 (7H, m), 7.83 (1H, d, J=15.6 Hz), 7.24 (4H, s), 7.13 (1H, d, J=8.1 Hz), 6.12 (1H, t, J=4.5 Hz), 2.42 (2H, d, J=4.8 Hz), 2.38 (3H, s), 1.41 (6H, s).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residual oil dissolved in EtOAc
  3. additionThe solution was treated with 10% HCl
  4. washthe organic layer was washed with H2O, and saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record
ord-683867a1e5004fc69d2514495e668a45
Source dataset
uspto-grants-1999_12
Patent number
US06008204

Reaction notes

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