Hydrochloric Acid → 4-n-Butyl-2-methoxybenzoic acid

HRID 1872704Notes

Reaction equation

HRID 1872704 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH3:13])=[CH:6][C:5]=1[O:14][CH3:15].Cl>CO.[OH-].[Na+]>[CH2:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[C:5]([O:14][CH3:15])[CH:6]=1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 545657104-n-Butyl-2-methoxybenzoic acid methyl ester

Product 1

HCID 186873724-n-Butyl-2-methoxybenzoic acidYield 72.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-bromo-2-methoxybenzoic acid methyl ester (3.0 g, 0.0122 mole), lithium chloride (1.56 g), tetra butyl tin (4.51 g) and bis (triphenyl phosphine palladium (II) chloride (214 mg, 0.3 mmol) were heated at 100° C. for 24h. The solvent was then removed in vacuo and the residue taken up in dichloromethane. The black solid was removed by filtration and the filtrate concentrated in vacuo to give a yellow oil. The oil was purified by column chromatography (Biotage) on silica gel using 10% ether in hexane to afford a colourless oil (1.63 g). A portion of the foregoing 4-n-butyl-2-methoxybenzoic acid methyl ester (1.50 g) was dissolved in methanol (35 ml) with sodium hydroxide solution (2N, 30 ml). The mixture was allowed to stir at room temperature overnight. Then added dil. HCl until pH-5. The solvent was then removed in vacuo and the residue taken up in ethyl acethate and washed with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford an oil (1.02 g).

Workup

  1. customThe solvent was then removed in vacuo
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-668c0532abeb4e8a89d7746da9c34d1f
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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