Phenacyl bromide → NSC678029

HRID 263955Notes

Reaction equation

HRID 263955 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:16]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][O:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][C:4](=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 546829304-Hydroxycoumarin

Product 1

HCID 386272NSC678029Yield 62.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-hydroxycoumarin (1.62 g, 10 mmol) in acetone (60 ml) were added 2-bromoacetophenone (1.99 g, 10 mmol) and potassium carbonate (5.53 g, 40 mmol). The mixture was refluxed for 3 h. (monitored by TLC). Evaporation of the solvent gave a residue which was poured into ice water (50 ml). The resulting solid was collected and crystallized from ethyl acetate to afford 4-(2-Oxo-2-phenylethoxy)-2H-1-benzopyran-2-one (2a) (1.76 g, 62.9%) as a needle crystal. mp: 183°-184° C.; IR(KBr) νmax : 1721, 1703, 1626; UV(CHCl3) λmax (log ε): 306 (3.79), 253 (4.28); 1H-NMR (CDCl3): δ5.50 (s, 2H, OCH2), 5.61 (s, 1H, 3-H), 7.26-7.35 (m, 2H, 6- and 8-H), 7.50-7.71 (m, 4H, 5-, 7-H and aromatic H), 7.94-8.02 (m, 3H, aromatic H). Anal. Calcd for C17H12O4 : C, 72.85; H, 4.32. Found: C, 72.85; H, 4.72.

Workup

  1. temperatureThe mixture was refluxed for 3 h. (monitored by TLC)
  2. customEvaporation of the solvent
  3. customgave a residue which
  4. customThe resulting solid was collected
  5. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b727ac0dc12f48d393a09749bbf1bc4b
Source dataset
uspto-grants-1997_07
Patent number
US05646164

Reaction notes

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