Hydrochloric Acid → HCID 11084884, compound

HRID 890952Notes

Reaction equation

HRID 890952 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]#N)[CH:9]=[CH:8]2.[OH-:15].[K+].Cl.C(O)C.[OH2:21]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([OH:21])=[O:15])[CH:9]=[CH:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 22243547HCID 22243547, compound

Product 1

HCID 11084884HCID 11084884, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 8-methoxy-2-naphthonitrile (263 mg, 1.44 mmol) and KOH (242 mg, 4.3 mmol) in 95% ethanol (5 mL) is heated to reflux for 72 hours. The solvent boiled off during heating leaving a solid. The reaction mixture is allowed to cool, dissolved in 1:1 ethanol-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 8-methoxy-2-naphthoic acid as a white solid (288 mg, 99%). HRMS (EI) calculated for C12H10O3: 202.0630, found 202.0629.

Workup

  1. temperatureto reflux for 72 hours
  2. temperatureduring heating
  3. customleaving a solid
  4. temperatureto cool
  5. filtrationThe resulting precipitate is collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9d69eeca18d048219583948f9af77915
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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