Dimethylformamide → Methyl 4-(4-oxo-4-phenylbutoxy)benzoate ethylene acetal

HRID 1585650

Reaction equation

HRID 1585650 reaction equation
[C:1]1([C:7]2([CH2:12][CH2:13][CH2:14]Cl)OCC[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](=[O:19])([O-])[O-].[K+].[K+].[OH:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1.[CH3:33]N(C)C=O>O>[CH2:16]1[O:19][C:27]([O:28][CH3:33])([C:26]2[CH:25]=[CH:24][C:23]([O:22][CH2:14][CH2:13][CH2:12][C:7](=[O:8])[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:32][CH:31]=2)[O:29][CH2:30]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 128663382-(3-Chloropropyl)-2-phenyl-1,3-dioxolane

Product 1

HCID 70111092Methyl 4-(4-oxo-4-phenylbutoxy)benzoate ethylene acetal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Crude 2-phenyl-2-(3-chloropropyl)-1,3-dioxolane (21.0 g), potassium carbonate (14.0 g; 0.101 moles) and methyl 4-hydroxybenzoate (14.0 g, 0.092 moles) were heated in dimethylformamide (100 ml) for 21 hours. The mixture was diluted with water (250 ml) and extracted with dichloromethane (500 ml). The dichloromethane extract was washed with saturated sodium bicarbonate solution and then with water. The organic extract was concentrated in vacuo to give the product as a brown solid (27.3 g).

Workup

  1. extractionextracted with dichloromethane (500 ml)
  2. extractionThe dichloromethane extract
  3. washwas washed with saturated sodium bicarbonate solution
  4. extractionThe organic extract
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-7132aa972471458f9d7cf03adf3145e6
Source dataset
uspto-grants-1999_08
Patent number
US05939447

Linked notes

Loading…