2-Hydroxy-4-methoxybenzophenone → HCID 69082653, compound

HRID 2205584Notes

Reaction equation

HRID 2205584 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].Br[CH2:19][CH2:20][CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+].[NH:29]([CH2:33][CH2:34][OH:35])[CH2:30][CH2:31][OH:32].[I-].[Na+]>O.CC(C)CC(=O)C>[OH:32][CH2:31][CH2:30][N:29]([CH2:33][CH2:34][OH:35])[CH2:19][CH2:20][CH2:21][O:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:11]

Participants

8

Reactant 5

HCID 46322-Hydroxy-4-methoxybenzophenoneHCID 5238Sodium IodideHCID 80061-Bromo-3-chloropropaneHCID 8113DiethanolamineHCID 11430Potassium Carbonate

Product 1

HCID 69082653HCID 69082653, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
120 °C

Procedure

A 500 mL three-neck flask was charged with (2-hydroxy-4-methoxyphenyl)(phenyl) methanone (100.0 g; 0.4381 mol), 1-bromo-3-chloropropane (82.78 g; 0.5258 mol) and 4-methyl-2-pentanone (250 mL). Anhydrous potassium carbonate (66.61 g; 0.4819 mol) was added and the reaction mixture was stirred at reflux (120° C.) for 10 h. The reaction mixture was filtered hot and the inorganic solids were washed with 4-methyl-2-pentanone (2×100 mL). The filtrate was charged into a mixture of neat diethanolamine (161.2 g; 1.533 mol) and sodium iodide (6.57 g; 43.81 mmol). The reaction mixture heated to reflux (122° C.) for 24 h. The reaction mixture was cooled to room temperature and diluted with water (500 mL). The resulting emulsion was extracted with 4-methyl-2-pentanone (2×200 mL). The aqueous phase was discarded and the organic phase was extracted with 1 M HCl (2×500 mL). The aqueous phase was taken to pH 12 with 50% aqueous NaOH. The resulting emulsion was extracted with 4-methyl-2-pentanone (3×200 mL). The organic phase was separated, dried (MgSO4), filtered and the solvent removed in vacuo. This provides (2-{3-[bis(2-hydroxyethyl)amino]propoxy}-4-methoxyphenyl)(phenyl)methanone (light yellow oil; 90.4 g; 55% yield over 3 steps).

Workup

  1. filtrationThe reaction mixture was filtered hot
  2. washthe inorganic solids were washed with 4-methyl-2-pentanone (2×100 mL)
  3. temperatureThe reaction mixture heated
  4. temperatureto reflux (122° C.) for 24 h
  5. temperatureThe reaction mixture was cooled to room temperature
  6. extractionThe resulting emulsion was extracted with 4-methyl-2-pentanone (2×200 mL)
  7. extractionthe organic phase was extracted with 1 M HCl (2×500 mL)
  8. extractionThe resulting emulsion was extracted with 4-methyl-2-pentanone (3×200 mL)
  9. customThe organic phase was separated
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d3ad43cfa0eb427caa0f42291d4dfc04
Source dataset
uspto-grants-2016_06
Patent number
US09371308B2

Reaction notes

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