Hydrochloric Acid → 7-Methoxynaphthalene-2-carboxylic acid

HRID 890946Notes

Reaction equation

HRID 890946 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]#N)=[CH:10]2)=[CH:5][CH:4]=1.[OH-:15].[K+].Cl.[OH2:18]>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]([OH:18])=[O:15])=[CH:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 109541837-Methoxy-2-naphthonitrile

Product 1

HCID 222432927-Methoxynaphthalene-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 7-methoxy-2-naphthonitrile (501 mg, 2.74 mmol) and KOH (503 mg, 9.0 mmol) in 95% ethanol (5 mL) is heated to reflux for 24 hours. The reaction mixture is allowed to cool, diluted with water and then acidified to pH<2 with concentrated HCl. The resulting precipitate is collected by filtration, washed with water and dried by heating at 70° C. under vacuum to give 7-methoxy-2-naphthoic acid as a white solid (540 mg, 98%). HRMS (FAB) calculated for C12H10O3+H+: 203.0708, found 203.0701.

Workup

  1. temperatureto reflux for 24 hours
  2. temperatureto cool
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b495e4e4b8e44840997a03d474959a16
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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