Hydrochloric Acid → 2,5-Dimethoxybenzoic acid

HRID 1632214Notes

Reaction equation

HRID 1632214 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1.[C:13]1(S(OC)(=O)=O)C=CC=CC=1.[H-].[Na+].[OH-].[Na+].Cl>C(O)C.O.CN(C)C=O>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6630Methyl benzenesulfonateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 757875-Methoxysalicylic Acid

Product 1

HCID 760272,5-Dimethoxybenzoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.05 g. (0.042 mole) of 5-methoxysalicyclic acid, 34.4 g. (0.2 mole) of methyl benzenesulfonate, 4.8 g. (0.2 mole) of sodium hydride and 100 ml. of N,N-dimethylformamide was heated at 125° C. for 16 hours, then poured into water. The mixture was extracted with diethyl ether and the extracts washed thrice with 200 ml. portions of 5N sodium hydroxide solution. The extracts were dried over magnesium sulfate, then evaporated to provide a residue which was dissolved in 100 ml. of ethanol and 100 ml. of 1N sodium hydroxide solution. The resulting solution was heated at reflux for 3 hours, then acidified with hydrochloric acid. The resulting solution was extracted with 200 ml. of diethyl ether. The extracts were washed with water, then dried. Evaporation provided 2,5-dimethoxybenzoic acid, m.p. 80°-85° C.

Workup

  1. additionA mixture of 7.05 g
  2. extractionThe mixture was extracted with diethyl ether
  3. washthe extracts washed thrice with 200 ml
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. customevaporated
  6. customto provide a residue which
  7. dissolutionwas dissolved in 100 ml
  8. temperatureThe resulting solution was heated
  9. temperatureat reflux for 3 hours
  10. extractionThe resulting solution was extracted with 200 ml
  11. washThe extracts were washed with water
  12. customdried
  13. customEvaporation

Sources & evidence

ORD record
ord-d19b2ef211154749bcdfc993eba03726
Source dataset
uspto-grants-1984_10
Patent number
US04474792

Reaction notes

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