Trifluoroacetic acid → 3-[2-(1-Naphthyl)ethoxy]propanoic acid

HRID 556715Notes

Reaction equation

HRID 556715 reaction equation
[C:1]1([CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67173567tert-Butyl 3-[2-(1-naphthyl)ethoxy]propanoate

Product 1

HCID 669337843-[2-(1-Naphthyl)ethoxy]propanoic acidYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-[2-(1-naphthyl)ethoxy]propanoate (6.19 g) was taken up in dichloromethane (30 mL) and treated with trifluoroacetic acid (5 mL). The resulting solution was stirred at room temperature for 2 hours, an additional 1 mL of trifluoroacetic acid was added and the solution stirred overnight. The mixture was concentrated, taken up in 2M sodium hydroxide solution (30 mL) and washed with ether (2×20 mL). The aqueous layer was subsequently acidified (using 1M hydrochloric acid) and extracted with ether (2×30 mL). The combined organics were washed with brine (20 mL), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the sub-titled compound (5.66 g) as a clear oil.

Workup

  1. stirringthe solution stirred overnight
  2. concentrationThe mixture was concentrated
  3. washwashed with ether (2×20 mL)
  4. extractionextracted with ether (2×30 mL)
  5. washThe combined organics were washed with brine (20 mL)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a12129f675ac4c7eb61918f07e60c979
Source dataset
uspto-grants-2011_11
Patent number
US08058294B2

Reaction notes

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