Hydrochloric Acid → 5-Methoxy-2-naphthoic acid

HRID 890949Notes

Reaction equation

HRID 890949 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:13]#N)=[CH:8]2.[OH-:15].[K+].Cl.[OH2:18]>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:13]([OH:18])=[O:15])=[CH:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 222435175-Methoxy-2-naphthonitrile

Product 1

HCID 129927605-Methoxy-2-naphthoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-methoxy-2-naphthonitrile (455 mg, 2.5 mmol) and KOH (460 mg, 8.2 mmol) in 95% ethanol (5 mL) is heated to reflux for 24 hours. The reaction mixture is allowed to cool, diluted with water 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 5-methoxy-2-naphthoic acid as a white solid (471 mg, 94%). HRMS (EI) calculated for C12H10O3: 202.0630, found 202.0627.

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-7ecc4aa7205542daa37ad2462f7c570c
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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