Trifluoroacetic acid → 4-(2-Ethoxycarbonylphenoxy)butyric acid

HRID 412707Notes

Reaction equation

HRID 412707 reaction equation
C([O:5][C:6]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(OCC)C>[CH2:17]([O:16][C:14]([C:13]1[CH:19]=[CH:20][CH:21]=[CH:22][C:12]=1[O:11][CH2:10][CH2:9][CH2:8][C:6]([OH:7])=[O:5])=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 18537757Ethyl 2-(3-tert-butoxycarbonylpropoxy)benzoate

Product 1

HCID 196227134-(2-Ethoxycarbonylphenoxy)butyric acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-(3-tert-butoxycarbonylpropoxy)benzoate (3.60 g, 11.7 mmol) was treated with an excess of trifluoroacetic acid at room temperature over one hour. The solution was concentrated in vacuo and the oily residue purified by silica gel flash chromatography using (10:1) hexane:ethyl acetate to pure ethyl ether to provide 4-(2-ethoxycarbonylphenoxy)butyric acid as a colorless crystalline solid (2.81 g, 95% yield); 1H NMR (300 MHz, CDCl3): 7.80 (d, 1H), 7.50 (tr, 1H), 7.00 (m, 2H), 4.40 (q, 2H), 4.15 (tr, 2H), 2.65 (tr, 2H), 2.20 (m, 2H), 1.40 (tr, 3H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe oily residue purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-2c1b868d5b6f49fc8f57fac738fa72fa
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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