Hydrochloric Acid → 2-Methoxy-1-naphthoic acid

HRID 1178300Notes

Reaction equation

HRID 1178300 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]([O:15]C)=[O:14].[OH-].[K+].CO.Cl>O.C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 604022Methyl 2-methoxy-1-naphthoate

Product 1

HCID 703562-Methoxy-1-naphthoic acidYield 67.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 21.6 g of the compound of Step A above in 48 ml of Claisen's alkali solution (solution of 21 g of KOH in 15 ml of water, made up to 60 ml with methanol) is heated at reflux for 4 hours. The reaction mixture is then diluted with 50 ml of water and poured into 75 ml of 15.5% hydrochloric acid solution cooled to 0° C. with stirring. The white precipitate formed is then filtered off over a Buchner funnel and then washed with water and dried under a phosphoric vacuum. The dry residue obtained is dissolved in a solution of ethanol and water (80:20, v/v) at boiling. After cooling to 0° C., 13.7 g of the expected product are obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. customThe white precipitate formed
  4. filtrationis then filtered off over a Buchner funnel
  5. washwashed with water
  6. customdried under a phosphoric vacuum
  7. customThe dry residue obtained
  8. temperatureAfter cooling to 0° C.

Sources & evidence

ORD record
ord-69dc9baf0c6746dda3fdcdb16b21c03a
Source dataset
uspto-grants-2007_10
Patent number
US07276512B2

Reaction notes

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