Acetic Acid → 4-Acetyl-2-methoxyphenyl acetate

HRID 1254163Notes

Reaction equation

HRID 1254163 reaction equation
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=[O:3].N1C=CC=CC=1.[C:19](O)(=[O:21])[CH3:20]>C1COCC1>[C:19]([O:10][C:9]1[CH:11]=[CH:12][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=1[O:7][CH3:8])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1049PyridineHCID 2214Acetovanillone

Product 1

HCID 5215354-Acetyl-2-methoxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As shown in the above-described reaction formula, acetovanillone (500 mg, 3 mM) dissolved in 20 ml of THF was mixed with 0.5 ml of pyridine and 0.6 ml of anhydrous acetic acid. The mixture was stirred for 3 hours at room temperature. The resulting product was recovered with the extraction with diethylether and dried with anhydrous magnesium sulfate to remove remaining solvent. The remaining residue was performed to Silica gel column chromatography with a mobile phase (n-hexane:ethylacetate=4:1) to obtain white solid type of 4-acetyl-2-methoxyphenyl acetate (1; 625 mg).

Workup

  1. customThe resulting product was recovered with the extraction with diethylether
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customto remove

Sources & evidence

ORD record
ord-0f232152983a4177af5cdba6cd5ae703
Source dataset
uspto-grants-2013_06
Patent number
US08455542B2

Reaction notes

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