Cesium carbonate → 1-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone

HRID 2267028Notes

Reaction equation

HRID 2267028 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[OH:12][C:13]1[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=1[C:23](=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[OH:12][C:13]1[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([O:22][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH:16]=[CH:15][C:14]=1[C:23](=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 684320061-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add 3-bromomethyl nitrobenzene (10.00 g, 46.3 mmol) to a solution of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (8.99 g, 46.3 mmol) in dimethylformamide (60 mL). After 10 minutes add potassium carbonate (9.60 g, 69.4 mmol) and cesium carbonate (15.08 g, 46.3 mmol). Stir at room temperature for one hour, then heat to 70° C. for 1.5 hours. Cool and add water (250 mL). Triturate for 15 minutes. Filter. Wash the solid with water several times, and then wash with hexanes. Dry to afford the title compound as an off white/light gray powder (12.9 g, 85%): 1H NMR (DMSO-d6) δ 0.91 (t, 3H), 1.52 (m, 2H), 2.58 (s, 3H), 2.63 (m, 2H), 5.42 (s, 2H), 6.72 (d, 1H), 7.73 (t, 1H), 7.83 (d, 1H), 7.90 (d, 1H), 8.21 (d, 1H), 8.34 (s, 1H), 12.88 (bs, 1H).

Workup

  1. temperatureheat to 70° C. for 1.5 hours
  2. temperatureCool
  3. customTriturate for 15 minutes
  4. filtrationFilter
  5. washWash the solid with water several times
  6. washwash with hexanes
  7. customDry

Sources & evidence

ORD record
ord-7af9434ab3fb455a94d0b8497cfc6ee5
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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