Carbon Dioxide → 5,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenecarboxylic acid

HRID 2288838Notes

Reaction equation

HRID 2288838 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=3)[C:11]([CH3:20])([CH3:19])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[C:26](=[O:28])=[O:27]>C1COCC1>[CH3:19][C:11]1([CH3:20])[CH2:10][CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:17]2[CH:16]=[C:15]([C:26]([OH:28])=[O:27])[CH:14]=[CH:13][C:12]1=2

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene2×HCID 178418306HCID 178418306, compound

Product 1

HCID 105416825,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene (Compound D) (250.0 mg, 0.764 mmol) in 2.0 ml of THF was cooled to -78° C. and 1.0 ml of t-butyllithium (1.68 mmol, 1.7 M solution in pentane) was added slowly. After stirring for 1 hour at -78° C. gaseous CO2 (generated by evaporation of Dry-Ice, and passed though a drying tube) was bubbled through the reaction for 1 hour. The solution was then allowed to warm to room temperature and the reaction was quenched by the addition of 10% HCl. Extraction with EtOAc was followed by washing the combined organic layers with H2O and saturated aqueous NaCl, and drying over MgSO4. Removal of the solvents under reduced pressure and washing of the solid with hexanes afforded the title compound as a colorless solid. 1H NMR (CDCl3): δ 7.94 (1H, dd, J=1.8, 8.1 Hz), 7.76 (1H, d, J=1.8 Hz), 7.45 (1H, d, J=8.1 Hz), 7.24 (4H, m), 6.01 (1H, t, J=4.7 Hz), 2.40 (3H, s), 2.36 (2H, d, J=4.7 Hz), 1.35 (6H, s).

Workup

  1. customwas bubbled through the reaction for 1 hour
  2. customthe reaction was quenched by the addition of 10% HCl
  3. extractionExtraction with EtOAc
  4. washby washing the combined organic layers with H2O and saturated aqueous NaCl
  5. dry with materialdrying over MgSO4
  6. customRemoval of the solvents under reduced pressure
  7. washwashing of the solid with hexanes

Sources & evidence

ORD record
ord-9a81770753c94a139da98c8e3dec550e
Source dataset
uspto-grants-2000_07
Patent number
US06090810

Reaction notes

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