tert-Butyl acrylate → HCID 22154047, compound

HRID 1110849Notes

Reaction equation

HRID 1110849 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])C=C.[C:20]([O-])(=[O:23])[CH:21]=C>[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:23][CH2:20][CH2:21][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:9])[C:11]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 15458tert-Butyl acrylateHCID 25188AcrylateHCID 953521-(4-Bromophenyl)ethanol

Product 1

HCID 22154047HCID 22154047, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

p-Bromophenylethanol is first condensed with t-butyl acrylate under conditions of the palladium acetate catalyzed Heck reaction. The resulting acrylate is hydrogenated with palladium on charcoal catalyst to yield t-butyl p-(2-hydroxyethyl)-phenylpropionate, which is converted to the corresponding tosylate by treatment with tosyl chloride in pyridine.

Sources & evidence

ORD record
ord-30beda62825e43cfa0cfe9436ea85ba8
Source dataset
uspto-grants-1990_12
Patent number
US04977144

Reaction notes

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