Methanol → Methyl 2,2-dimethyl-3-(3-benzyloxyphenyl)propionate

HRID 902712Notes

Reaction equation

HRID 902712 reaction equation
[CH3:1][C:2]([CH3:21])([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)[C:3]([OH:5])=[O:4].[CH3:22]O>OS(O)(=O)=O.O>[CH3:1][C:2]([CH3:21])([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)[C:3]([O:5][CH3:22])=[O:4]

Participants

5

Reactant 2

HCID 887MethanolHCID 688617242,2-Dimethyl-3-(3-benzyloxyphenyl)propionic Acid

Product 1

HCID 68861760Methyl 2,2-dimethyl-3-(3-benzyloxyphenyl)propionateYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2,2-dimethyl-3-(3-benzyloxyphenyl)propionic acid (400 mg, 1.4 mmole) in 20 mL of MeOH and 0.5 mL conc. H2SO4 was refluxed for 18 hours. The reaction was cooled, diluted with H2O and extracted with Et2O. The extracts were washed with H2O, three times with aqueous NaHCO3, dried, and the solvent evaporated. The residue was chromatographed over a silica gel column, and elution with a mixture of CH2Cl2, hexane and MeOH (50:50:1) gave the titled compound, 208 mg (50% yield). MS (ESI) 299 (MH+).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with Et2O
  3. washThe extracts were washed with H2O, three times with aqueous NaHCO3
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was chromatographed over a silica gel column, and elution with a mixture of CH2Cl2, hexane and MeOH (50:50:1)

Sources & evidence

ORD record
ord-dce5f7c2cfe044a5a8d85e98d8fda65e
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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