tert-Butyl (2E)-3-[2-(benzyloxy)-4-(trifluoromethyl)phenyl]acrylate → tert-Butyl 3-[2-hydroxy-4-(trifluoromethyl)phenyl]propanoate

HRID 910830Notes

Reaction equation

HRID 910830 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1/[CH:19]=[CH:20]/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:11][C:10]=1[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

4

Reactant 1

HCID 86620102tert-Butyl (2E)-3-[2-(benzyloxy)-4-(trifluoromethyl)phenyl]acrylate

Product 1

HCID 86620101tert-Butyl 3-[2-hydroxy-4-(trifluoromethyl)phenyl]propanoateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product from step (iv) (3.25 g) and 10% palladium on carbon (0.325 g) in ethanol (40 ml) was hydrogenated at a pressure of 3.0 bar overnight. The mixture was filtered through celite and the filtrate concentrated under reduced pressure to give a white solid (2.22 g).

Workup

  1. customwas hydrogenated at a pressure of 3.0 bar overnight
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-b16f6ae15ad3440bafeb67cd56eb5e20
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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