Hydrogen Peroxide → 2,5-Dimethoxyphenyl acetate

HRID 1159425Notes

Reaction equation

HRID 1159425 reaction equation
[CH3:1][C:2]([O:4][Na])=[O:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1C(=O)C.OO.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.CCOCC.O>[C:2]([O:4][C:12]1[CH:13]=[C:8]([O:7][CH3:6])[CH:9]=[CH:10][C:11]=1[O:14][CH3:15])(=[O:3])[CH3:1]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 709912',5'-DimethoxyacetophenoneHCID 178418247HCID 178418247, compound

Product 1

HCID 5874512,5-Dimethoxyphenyl acetateYield 787.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

CH3COONa (0.7 g, 0.009 mol) was added under stirring to a solution of 2′,5′-dimethoxyacetophenone (CAS 1201-38-3, 45 g, 0.25 mol) in acetic acid (50 mL). A 50% solution of H2O2 in H2O (43 g, 0.62 mol) was added dropwise at 40° C. The reaction mixture was stirred at 40° C. for 144 h. Then it was cooled, diluted with ether (150 mL) and H2O (100 mL), and alkalized to pH 6 with a saturated solution of K2CO3. The layers were separated. The organic one was washed with water (2×100 mL), brine, dried, and evaporated. The residue was recrystallized from ether to give the title compound (13.9 g, 28%) as white crystals. LCMS data: 197.0 (M+H)+ and 155.1, 156.1 (M-Ac+H) (calculated for C10H12O4 196.2). 1H NMR data (DMSO-d6): 7.04 (d, 1H, J=9.0 Hz, Ar—H), 6.80 (dd, 1H, J1=3.2 Hz, J2=9.0 Hz, Ar—H), 6.72 (d, 1H, J=2.9 Hz, Ar—H), 3.70 (s, 3H, —OCH3), 3.69 (s, 3H, —OCH3), 2.24 (s, 3H, —COCH3).

Workup

  1. temperatureThen it was cooled
  2. customThe layers were separated
  3. washThe organic one was washed with water (2×100 mL), brine
  4. customdried
  5. customevaporated
  6. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-64057bf89d2a45ae800ceac0d9a8f0d5
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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