Hydrochloric Acid → HCID 54295083, compound

HRID 1955568Notes

Reaction equation

HRID 1955568 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=3)[C:10]([CH3:21])([CH3:20])[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:22]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=O.[OH-].[Na+].Cl>CCO.C1COCC1>[O:19]=[C:17]([C:13]1[CH:14]=[CH:15][C:16]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH2:9][C:10]([CH3:21])([CH3:20])[C:11]=2[CH:12]=1)[CH:18]=[CH:22][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 120884-Formylbenzoic acidHCID 14798Sodium HydroxideHCID 22323722HCID 22323722, compound2×

Product 1

HCID 54295083HCID 54295083, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 115.0 mg (0.42 mmol) of 3,4-dihydro-1-phenyl-4,4-dimethyl-6-acetylnaphthalene (Compound 100H) and 65.0 mg (0.43 mmol) of 4-formyl-benzoic acid in 5.0 ml EtOH and 1.0 ml THF, was added 120.0 mg (3.00 mmol; 3.0 ml of a 1M aqueous solution) of NaOH. The resulting yellow solution was stirred at room temperature for 12 hours. The solution was acidified with 6% aqueous HCl and extracted with EtOAc. The combined organic layers were dried (MgSO4), concentrated under reduced pressure, and the title compounds was isolated by column chromatography (50% EtOAc--hexanes) as a pale yellow solid. 1H NMR (CDCl3): δ 8.13 (2H, d, J=7.7 Hz), 8.04 (1H, s), 7.81 (1H, d, J=15.5 Hz), 7.75 (3H, m), 7.60 (1H, d, J=15.5 Hz), 7.35 (5H, m), 7.14 (1H, d, J=8.1 Hz), 6.15 (1H, t, J=4.2 Hz), 2.41 (2H, d, J=4.2 Hz), 1.41 (6H, s).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63e1f8c65d0d4293869eab58ba4f681f
Source dataset
uspto-grants-1998_07
Patent number
US05776699

Reaction notes

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