Dimethylformamide → 4-Butoxy-2-methoxybenzoic acid

HRID 1632211Notes

Reaction equation

HRID 1632211 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH3:22].CN(C)C=O>O>[CH2:19]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1)[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 126955754-Hydroxy-2-methoxybenzoic acid

Product 1

HCID 64834054-Butoxy-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.2 g. (0.025 mole) of 4-hydroxy-2-methoxybenzoic acid, 7 g. of potassium carbonate, and 10 g. of n-butyl bromide in 100 ml. of N,N-dimethylformamide was heated at 70° C. for 24 hours. The mixture was cooled, diluted with water and extracted with diethyl ether. The ether extracts were washed with dilute sodium hydroxide solution, then washed with water and dried. The ether was evaporated and the residue heated at reflux for 4 hours in an equivolume mixture of 10 percent sodium hydroxide solution and ethanol. Evaporation followed by acidification provided the desired 4-(n-butoxy)-2-methoxy-benzoic acid (m.p. 94°-96° C. after recrystallizaiton from cyclohexane).

Workup

  1. additionA mixture of 4.2 g
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethyl ether
  4. washThe ether extracts were washed with dilute sodium hydroxide solution
  5. washwashed with water
  6. customdried
  7. customThe ether was evaporated
  8. temperaturethe residue heated
  9. temperatureat reflux for 4 hours in an equivolume mixture of 10 percent sodium hydroxide solution and ethanol
  10. customEvaporation

Sources & evidence

ORD record
ord-e73010d325434e25ae6972684bbc7982
Source dataset
uspto-grants-1984_10
Patent number
US04474792

Reaction notes

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