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

HRID 2298991Notes

Reaction equation

HRID 2298991 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:15]([O:17]C)=[O:16].[OH-].[K+]>O1CCOCC1.CO>[CH3:14][O:13][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH:1]=[C:2]([C:15]([OH:17])=[O:16])[CH:3]=[CH:4]2)=[O:12]

Participants

5

Reactant 2

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

Product 1

HCID 33802176-(Methoxycarbonyl)naphthalene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of dimethyl 2,6-naphthalenedicarboxylate (39.6 g, 162 mmol) in dioxane (1.2 L) was heated to 70-80° C., slowly treated with a solution of KOH (9.1 g, 162 mmol) in methanol (162 mL), heated to 70° C., stirred for 30 minutes, cooled to room temperature, and filtered. The solid was washed sequentially with dioxane and diethyl ether, dissolved in water, adjusted to pH<7 with 1M HCl, and filtered. The solid was washed with water and dried to provide the desired product.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed sequentially with dioxane and diethyl ether
  4. dissolutiondissolved in water
  5. filtrationfiltered
  6. washThe solid was washed with water
  7. customdried

Sources & evidence

ORD record
ord-76ae99376acd46b086f59ffa9e0112c2
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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