Trifluoroacetic acid → 4-(tetrahydrofuran-3-yl)benzoic acid

HRID 1500956Notes

Reaction equation

HRID 1500956 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:18]=[CH:17][C:9]([C:10]([O:12]C(C)(C)C)=[O:11])=[CH:8][CH:7]=2)[CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:18]=[CH:17][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89580621HCID 89580621, compound

Product 1

HCID 838300274-(tetrahydrofuran-3-yl)benzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(tetrahydrofuran-3-yl)benzoate (350 mg, 1.41 mmol) was added trifluoroacetic acid (2 mL) in dichloromethane (10 mL) and then stirred at room temperature for 0.5 hour. Solvent concentration gave final desired product 4-(tetrahydrofuran-3-yl)benzoic acid (200 mg, 74%) as a white solid. LRMS (M−H+) m/z: calcd 192.08. found 192.

Workup

  1. concentrationSolvent concentration

Sources & evidence

ORD record
ord-d3035d7b594b4c10ae9e1e87d27b7cea
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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