Trifluoroacetic acid → HCID 19900649, compound

HRID 2104293Notes

Reaction equation

HRID 2104293 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])[O:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])([CH3:11])([CH3:10])[CH3:9]>ClCCl>[C:8]([C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])[O:15][CH2:16][C:17]([OH:19])=[O:18])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22711584HCID 22711584, compound

Product 1

HCID 19900649HCID 19900649, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.6 ml (46 mmol) of trifluoroacetic acid is added to a solution of 1.56 g (4.64 mmol) of tert-butyl 2-[3,5-di(tert-butyl)-4-hydroxyphenoxy]acetate (prepared according to J. Heterocycl. Chem. (1994) 31, 1439-1443) in 20 ml of dichloromethane. The reaction mixture is agitated for 1 hour, concentrated under vacuum and the residue is dissolved in 50 ml of Et2O. The organic solution is extracted twice with 25 ml of a saturated solution of NaHCO3, the aqueous phase is then washed with 25 ml of Et2O. The basic aqueous solution is then acidified, at 0° C., with a saturated solution of KHSO4 and finally the expected product is extracted using twice 25 ml of Et2O. The organic solution is dried over sodium sulphate, filtered and concentrated under vacuum in order to produce a white powder with a yield of 70%. Melting point: 172-173° C.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionthe residue is dissolved in 50 ml of Et2O
  3. extractionThe organic solution is extracted twice with 25 ml of a saturated solution of NaHCO3
  4. washthe aqueous phase is then washed with 25 ml of Et2O
  5. customis then acidified, at 0° C., with a saturated solution of KHSO4
  6. extractionfinally the expected product is extracted
  7. dry with materialThe organic solution is dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum in order
  10. customto produce a white powder with a yield of 70%

Sources & evidence

ORD record
ord-b0b40f82628c419c8aad23ec8b5adf23
Source dataset
uspto-grants-2009_08
Patent number
US07576241B2

Reaction notes

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