Acetone → HCID 69005679, compound

HRID 734187Notes

Reaction equation

HRID 734187 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[OH:16])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:23](Br)[CH:24]=[CH2:25].[CH3:27][C:28]([CH3:30])=O>>[CH2:23]([O:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH2:30][CH:28]=[CH2:27])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])[CH:24]=[CH2:25]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 10796Cesium carbonate2×HCID 165870Methanone, (3,4-dihydroxyphenyl)phenyl-

Product 1

HCID 69005679HCID 69005679, compoundYield 99%

Conditions

Temperature
60 °C

Procedure

To a suspension of 3,4-dihydroxybenzophenone (2.140 g, 10 mmol) and cesium carbonate (7.010 g, 21.6 mmol) in dry acetone (50 mL) was added allylbromide (5.3 mL, 60 mmol). The mixture was stirred at 60° C. for 6 h and additional allybromide (3.0 mL, 34.7 mmol) and cesium carbonate (3.000 g, 9.2 mmol) were added. The mixture was stirred for 3 h, cooled to room temperature, filtered and washed with EtOAc. The filtrate and washing were combined and evaporated under reduced pressure. The crude product was partitioned between EtOAc (50 mL) and H2O (15 mL). The EtOAc phase was separated and evaporated to give a light yellow oil (2.922 g, 99%): 1H NMR (CDCl3, 300 MHz) δ 7.77 (m, 1H), 7.74 (m, 1H), 7.57 (m, 1H), 7.50-7.44 (m, 3H), 7.38 (ddd, J=0.9, 2.4, 8.7 Hz, 1H), 6.91 (d, J=8.4 Hz, 1H), 6.08 (m, 2H), 5.47 (m, 1H), 5.41 (m, 1H), 5.32 (m, 2H), 4.68 (m, 4H).

Workup

  1. stirringThe mixture was stirred for 3 h
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washwashed with EtOAc
  5. washThe filtrate and washing
  6. customevaporated under reduced pressure
  7. customThe crude product was partitioned between EtOAc (50 mL) and H2O (15 mL)
  8. customThe EtOAc phase was separated
  9. customevaporated

Sources & evidence

ORD record
ord-45f109c9251d4fd28cc081b94b916bff
Source dataset
uspto-grants-2009_09
Patent number
US07592143B2

Reaction notes

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