Potassium Hydroxide → 6-(Methoxycarbonyl)naphthalene-2-carboxylic acid

HRID 2422947Notes

Reaction equation

HRID 2422947 reaction equation
[OH-].[K+].[CH:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:17]([O:19]C)=[O:18]>CO.O1CCOCC1>[CH3:16][O:15][C:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[CH:3]=[C:4]([C:17]([OH:19])=[O:18])[CH:5]=[CH:6]2)=[O:14]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 61225Dimethyl-2,6-naphthalenedicarboxylate

Product 1

HCID 33802176-(Methoxycarbonyl)naphthalene-2-carboxylic acidYield 82.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of KOH (0.459 g, 8.18 mmol) in methanol (1.5 ml) was added to a suspension of dimethyl 2,6-naphthlene dicarboxylate (2.0 g, 8.18 mmol) in dioxane (20 ml). The reaction mixture was stirred at 80° C. for 4 h, cooled to room temperature and a solid residue was rinsed with diethyl ether (10 ml). The solid was dissolved in water and treated with HCl (aq, 2M) to pH 3. The precipitate was filtered, washed with water, dried under vacuum to provide pure 74 as a white solid (1.55 g, 6.72 mmol, 82%). 1H NMR (400 MHz, DMSO-d6) δ 3.91 (3H, s), 8.02 (2H, dd, J 8.4 Hz), 8.22 (2H, dd, J 8.4 Hz), 8.66 (2H, dd, J 10.4 Hz).

Workup

  1. temperaturecooled to room temperature
  2. washa solid residue was rinsed with diethyl ether (10 ml)
  3. dissolutionThe solid was dissolved in water
  4. additiontreated with HCl (aq, 2M) to pH 3
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5a9e81928724485ebd358021d2229a17
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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