Trifluoroacetic acid → HCID 90282105, compound

HRID 1497525Notes

Reaction equation

HRID 1497525 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[C:11]([Cl:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[C:11]([Cl:24])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90281930HCID 90281930, compound

Product 1

HCID 90282105HCID 90282105, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[4-(benzyloxy)-2-chlorophenyl]propanoate (22.5 g) in dichloromethane (67.6 mL) was added trifluoroacetic acid (24.8 mL), followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 3-[4-(benzyloxy)-2-chlorophenyl]propanoic acid (13.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a48c2b3e4b6449b5a1091234640a4e12
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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