Acetic Anhydride → WS-5995 A

HRID 1648945Notes

Reaction equation

HRID 1648945 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:13])[C:4](=[O:14])[C:3]=1[C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([CH3:26])=[CH:20][C:16]=1[C:17](O)=[O:18].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OC(=O)C)(=O)C>C(OCC)(=O)C>[OH:13][C:9]1[C:10]2[C:11](=[O:12])[C:2]3[O:1][C:17](=[O:18])[C:16]4[CH:20]=[C:21]([CH3:26])[CH:22]=[C:23]([O:24][CH3:25])[C:15]=4[C:3]=3[C:4](=[O:14])[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9845Trifluoroacetic anhydrideHCID 178490201HCID 178490201, compound

Product 1

HCID 156387WS-5995 A

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The entire amount of the 2-(3,5-dihydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoic acid obtained above was dissolved in ethyl acetate (10 ml) and while the solution was stirred at room temperature, a mixture (1 ml:10 ml) of trifluoroacetic anhydride and acetic anhydride was added. The mixture was further stirred at the same temperature for an hour. This reaction mixture was washed with water and dilute aqueous sodium carbonate in that order, followed by drying over magnesium sulfate. The solvent was then distilled off and the residual brown oil was subjected to silica gel column chromatography to give vermillion-colored crystals (20 mg).

Workup

  1. stirringThe mixture was further stirred at the same temperature for an hour
  2. washThis reaction mixture was washed with water and dilute aqueous sodium carbonate in that order
  3. dry with materialby drying over magnesium sulfate
  4. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-49de84f189fc489eb8cd3c29f3853600
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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