Hydrochloric Acid → Methyl 3-[(4-ethylphenyl)methyl]-4-hydroxybenzoate

HRID 1297542Notes

Reaction equation

HRID 1297542 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1)[CH3:2].Cl.C[OH:23]>[C].[Pd]>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=2[OH:23])[C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 69200004HCID 69200004, compound

Product 1

HCID 23072810Methyl 3-[(4-ethylphenyl)methyl]-4-hydroxybenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

The thus obtained methyl 3-[(4-ethylphenyl)hydroxymethyl]benzoate (2.88 g, 10.0 mmol), 10% palladium carbon (200 mg), concentrated hydrochloric acid (0.5 mL) and methanol (15 mL) were mixed and stirred under a hydrogen atmosphere at room temperature for 14 hours. After filtration to remove the insoluble materials, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to give methyl 3-(4-ethylbenzyl)-4-hydroxybenzoate (2.38 g, 88%) as a colorless powder.

Workup

  1. filtrationAfter filtration
  2. customto remove the insoluble materials
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-ba7072b3e45a43588f3c7eaedd700111
Source dataset
uspto-grants-2007_07
Patent number
US07250522B2

Reaction notes

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