Potassium Carbonate → Ethyl 2-(4-acetyl-2-methylphenoxy)acetate

HRID 9700

Reaction equation

HRID 9700 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](S)=[CH:9][C:8]=1[CH3:14])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[C:23](C)(C)[C:24](OCC)=[O:25]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:24](=[O:25])[CH3:23])=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetate

Product 1

HCID 21986544Ethyl 2-(4-acetyl-2-methylphenoxy)acetateYield 159%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To intermediate 4 (710 mg, 1.81 mmol) in DMF (50 mL) was added the K2CO3 (275 mg, 1.99 mmol) followed by the ethyl 2-bromo-2-methylpropanate (280 μL, 1.91 mmol; Aldrich) and the reaction heated to 80° C. After 18 h, the reaction cooled to rt and the solvent removed in vacuo. The residue treated with water (200 mL), extracted 3×50 mL CH2Cl2, dried over Na2SO4, filtered and the solvent removed under vaccum. The residue was chromatographed (CH2Cl2/MeOH: 99/1). To afford 680 mg (77%) of Intermediate 5 as a clear oil. 1H NMR(CDCl3): δ 7.95 (d, 2H), 7.60 (d, 2H), 7.15 (d, 2H), 6.75 (d, 2H), 6.05 (t, 1H), 4.45 (d, 2H), 4.15 (q, 2H), 2.65 (s, 3H), 1.50 (s, 6H), 1.20 (t, 3H).

Workup

  1. temperaturethe reaction cooled to rt
  2. customthe solvent removed in vacuo
  3. additionThe residue treated with water (200 mL)
  4. extractionextracted 3×50 mL CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed under vaccum
  8. customThe residue was chromatographed (CH2Cl2/MeOH: 99/1)

Sources & evidence

ORD record
ord-ef292f5548cf455d9ca50f896ef61a98
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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