Acetic Acid → 2',3'-Dihydroxyacetophenone

HRID 38630

Reaction equation

HRID 38630 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][C:10](O)=[O:11].B(F)(F)F.CCOCC>ClCCl.O>[CH3:9][C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:1]([OH:2])[C:3]=1[OH:4])=[O:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 289CatecholHCID 8000Boron trifluoride etherate

Product 1

HCID 64291102',3'-DihydroxyacetophenoneYield 10.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1,2-dihydroxybenzene (28)(2.0 g, 18.2 mmol) in AcOH (1.3 g, 21.7 mmol) was added boron trifluoride diethyl ether (98% in Et2O, 2 mL). The mixture was reacted under microwave irradiation (300 W) for 1.5 min and then cooled to 25° C. The reaction mixture was dissolved in dichoromethane (10 mL) and H2O (about 20 mL). The organic lay was washed with 10% NaHCO3 and then with water, dried over MgSO4 and concentrated. The crude was purified by column chromatography (SiO2, CH2Cl2) to give 30. Yellow solid; yield: 10.4%; mp 76-77° C.; 1H-NMR (CDCl3,200 MHz): δ 2.58 (s, 3H), 5.79 (s, 1H), 6.79 (t, J=8.0 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 12.45 (s, 1H); 13C-NMR (CDCl3, 50 MHz): δ 26.73, 118.79, 119.52, 120.39, 121.44, 145.40, 149.50, 205.08; Anal. calcd for C8H8O3: C, 63.15; H, 5.30. Found: C, 63.10; H, 5.33.

Workup

  1. customThe mixture was reacted under microwave irradiation (300 W) for 1.5 min
  2. washThe organic lay was washed with 10% NaHCO3
  3. dry with materialwith water, dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude was purified by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-535d1541544642f3a85aeeb50cc10816
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Linked notes

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