Acetone → HCID 53719404, compound

HRID 613045Notes

Reaction equation

HRID 613045 reaction equation
C[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[CH3:12]C(C)=O.C[O:17][C:18](=[O:21])[CH2:19]Br>O>[C:18]([O:21][O:11][C:8]1[CH:7]=[CH:6][C:5]([C:3](=[O:4])[CH3:2])=[CH:10][C:9]=1[CH3:12])(=[O:17])[CH3:19]

Participants

5

Reactant 3

HCID 180AcetoneHCID 62714'-HydroxypropiophenoneHCID 60984Methyl bromoacetate

Product 1

HCID 53719404HCID 53719404, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxypropiophenone (10.0 g, 60.24 mmol), CsCO3 (21.6 g, 66.3 mmol), and acetone (150.0 mL) under an N2 atmosphere was treated with methylbromoacetate (7.26 mL, 78.3 mmol) and the mixture heated to reflux for 4 h. The mixture was then allowed to cool to ambient temperature, diluted with H2O (150 mL) and extracted with CH2Cl2 (2×300 mL). The organic layers were combined, dried with Na2SO4, and the solvent removed in vacuo to provide the title compound (12.75 g, m.p. 64-66° C.). 1H NMR (400 MHz, DMSO-d6) δ9.35 (d, 2 H, J=8.9 Hz), 7.040 (d, 2 H, J=8.9 Hz), 4.920 (s, 2 H), 3.715 (s, 3 H), 2.981 (q, 2 H, J=7.2 Hz), 1.071 (t, 3 H, J=7.2 Hz).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h
  3. extractionextracted with CH2Cl2 (2×300 mL)
  4. dry with materialdried with Na2SO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b992b7d0de124cec826ef04b5dd2c671
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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