Hydrochloric Acid → Benzyl 2-benzyloxy-4-trifluoromethanesulfonyloxybenzoate

HRID 30733Notes

Reaction equation

HRID 30733 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16]([O:23][C:24]1[CH:39]=[C:38](O)[CH:37]=[CH:36][C:25]=1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[CH2:16]([O:23][C:24]1[CH:39]=[C:38]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:37]=[CH:36][C:25]=1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 23090785Benzyl 2-benzyloxy-4-hydroxybenzoate

Product 1

HCID 23090750Benzyl 2-benzyloxy-4-trifluoromethanesulfonyloxybenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.22 mL) was added to an ice-cooled mixture of benzyl 2-benzyloxy-4-hydroxybenzoate (0.40 g) and pyridine (0.1 mL) in methylene chloride (1.5 mL) with stirring, and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into a mixture of hydrochloric acid and ethyl acetate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure liquid silica gel column chromatography (eluent: n-hexane/ethyl acetate=6/1) to afford benzyl 2-benzyloxy-4-trifluoromethanesulfonyloxybenzoate (0.56 g).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by medium-pressure liquid silica gel column chromatography (eluent: n-hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-800e894c58404c6eb26e1575993b45cb
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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