HCID 4739258, compound → HCID 67599519, compound

HRID 1417101Notes

Reaction equation

HRID 1417101 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([CH3:15])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:17][C:18](C)([O-])C.[K+].Br[CH2:24][C:25]1[C:26]([C:31]([O-:33])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=1>CN(C)C=O>[CH2:17]([O:33][C:31](=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:16])([CH3:15])[CH3:14])=[CH:12][CH:11]=1)[CH3:18]

Participants

5

Reactant 3

HCID 4739258HCID 4739258, compoundHCID 23665647Potassium tert-butoxideHCID 461805253-(4-Hydroxyphenyl)-2,2-dimethylpropanoic acid ethyl ester

Product 1

HCID 67599519HCID 67599519, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(4-hydroxyphenyl)-2,2-dimethylpropanoic acid ethyl ester (12.2 g) was added to a slurry containing 6.46 g of potassium tert-butoxide in 55 ml dry dimethylformamide at 0° C. After 30 minutes, a solution containing 12.6 g of ethyl (α-bromo-ortho-toluate in 15 ml dry dimethylformamide was added and the solution stirred for 2 hours at room temperature, then at 50° C. overnight. Dilution with water, extraction with ether and evaporation left an oil which was purified by HPLC (silica gel, 7:3 dichloromethane-heptane) to give 20.3 g of 2-[4-(2-ethoxycarbonyl-2-methylpropyl)phenoxymethyl]benzoic acid ethyl ester as an oil.

Workup

  1. additionwas added
  2. customat 50° C.
  3. customovernight
  4. extractionDilution with water, extraction
  5. customwith ether and evaporation
  6. waitleft an oil which
  7. customwas purified by HPLC (silica gel, 7:3 dichloromethane-heptane)

Sources & evidence

ORD record
ord-0940ae994d7a469588b7f94a6c64d643
Source dataset
uspto-grants-1999_06
Patent number
US05917057

Reaction notes

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