Iodine → 3-(4-Hydroxyphenyl)-2,2-dimethylpropanoic acid ethyl ester

HRID 1417100Notes

Reaction equation

HRID 1417100 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)(=O)C.II>C1(C)C=CC=CC=1.[Zn].[Pd]>[CH2:6]([O:5][C:3](=[O:4])[C:2]([CH3:9])([CH3:8])[CH2:18][C:17]1[CH:16]=[CH:15][C:14]([OH:13])=[CH:21][CH:20]=1)[CH3:7]

Participants

7

Reactant 3

HCID 807IodineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 70144Benzaldehyde, 4-(acetyloxy)-

Product 1

HCID 461805253-(4-Hydroxyphenyl)-2,2-dimethylpropanoic acid ethyl esterYield 14.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23994ZincCatalystHCID 1140TolueneSolvent2×

Procedure

A slurry containing 24.6 g of zinc dust in 100 ml dry toluene was treated dropwise with a solution containing 73.5 g of ethyl bromoisobutyrate and 65 g of 4-acetoxybenzaldehyde in 200 ml dry toluene. A crystal of iodine was added to initiate the reaction and the mixture was heated to reflux overnight. An additional equivalent of ethyl bromoisobutyrate was added and reflux was continued for 24 hours. After cooling, the filtrate was hydrogenated over palladium and the residue purified by flash chromatography to give 12.2 g of 3-(4-hydroxyphenyl)-2,2-dimethylpropanoic acid ethyl ester as an oil.

Workup

  1. additionwas treated dropwise with a solution
  2. customthe reaction
  3. temperaturethe mixture was heated
  4. temperatureto reflux overnight
  5. temperaturereflux
  6. temperatureAfter cooling
  7. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-7f5059bfc63a4f7c8c201eff0253daba
Source dataset
uspto-grants-1999_06
Patent number
US05917057

Reaction notes

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