Diethyl Ether → Methyl 2-ethoxy-4-(1-hydroxy-2-methylpropan-2-yl)benzoate

HRID 2425586Notes

Reaction equation

HRID 2425586 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11]1[CH:16]=[C:15]([C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])[CH:14]=[CH:13][C:12]=1[I:22])[CH3:9].[C]=[O:24].C[CH2:26][O:27][CH2:28]C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:8]([O:10][C:11]1[CH:16]=[C:15]([C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])[CH:14]=[CH:13][C:12]=1[C:26]([O:27][CH3:28])=[O:24])[CH3:9].[CH2:8]([O:10][C:11]1[CH:16]=[C:15]([C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])[CH:14]=[CH:13][C:12]=1[I:22])[CH3:9]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 67244628HCID 67244628, compoundHCID 178418416HCID 178418416, compound2×

Product 2

HCID 53412311Methyl 2-ethoxy-4-(1-hydroxy-2-methylpropan-2-yl)benzoateYield 48%HCID 67244628HCID 67244628, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

Triethylamine (3.5 mL, 25.1 mmol) was added to a solution 2-ethoxy-4-(2-hydroxy-1,1-dimethylethyl)iodobenzene (4.0 g, 12.5 mmol) in methanol (20 mL) under an atmosphere of nitrogen. The reaction was purged twice with carbon monoxide, and palladium (II) acetate (0.2 g, 0.9 mmol) was added. The reaction was stirred at 80° C. for 18 h under a positive pressure of carbon monoxide. The reaction was diluted with ether, washed with 10% hydrochloric acid, aqueous sodium bicarbonate, brine, dried over anhydrous magnesium sulfate and concentrated. Purification of the crude residue by flash chromatography over silica gel using 20-75% ethyl acetate in hexanes gave methyl 2-ethoxy-4-(2-hydroxy-1,1-dimethylethyl)benzoate (1.5 g, 48%) as a yellow oil and 0.91 g of unreacted 2-ethoxy-4-(2-hydroxy-1,1-dimethylethyl)iodobenzene.

Workup

  1. additionwas added
  2. washwashed with 10% hydrochloric acid, aqueous sodium bicarbonate, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the crude residue by flash chromatography over silica gel using 20-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bd290047cb9644e0b28fcc4ddda7df94
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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