Trifluoroacetic acid → 2-(2-(Benzyloxy)ethoxy)acetic acid

HRID 468600Notes

Reaction equation

HRID 468600 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)CCC.C(O)(C(F)(F)F)=O>ClCCl>[CH2:12]([O:11][CH2:10][CH2:9][O:8][CH2:7][C:6]([OH:19])=[O:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731128Butyl[2-(benzyloxy)ethoxy]acetate

Product 1

HCID 217901362-(2-(Benzyloxy)ethoxy)acetic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ester 9 (2.66 g, 10 mmol) in dichloromethane (91 ml) was added TFA (9 ml) reaction mixture was stirred at room temperature for 2 hrs and mixture was concentrated. Obtained residue was diluted in water and basified with a NaOH 1N solution. This aqueous layer was extracted with ether then acidified and extracted twice with EtOAc. Combined organic layers were dried over MgSO4, filtered and concentrated to give acid 10 (2 g, 95%) as an oil, used for next step without further purification.

Workup

  1. concentrationmixture was concentrated
  2. additionObtained residue was diluted in water
  3. extractionThis aqueous layer was extracted with ether
  4. extractionextracted twice with EtOAc
  5. dry with materialCombined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-18f059ec4e394ed4a143aabcbc9df68f
Source dataset
uspto-grants-2014_01
Patent number
US08624044B2

Reaction notes

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