Diisopropyl Ether → Ethyl 2-(4-Chlorophenyl)-5,5-diphenyl[1,3]-dioxane-2-carboxylate

HRID 1859758Notes

Reaction equation

HRID 1859758 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:15]1([C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:24]O)[CH2:22][OH:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.B(F)(F)F.CCOCC.C(OC(C)C)(C)C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([C:2]2([C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:23][CH2:22][C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:24][O:1]2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8000Boron trifluoride etherateHCID 4104452,2-Diphenylpropane-1,3-diolHCID 2758815Ethyl 4-chlorobenzoylformate

Product 1

HCID 15428824Ethyl 2-(4-Chlorophenyl)-5,5-diphenyl[1,3]-dioxane-2-carboxylateYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

42.5 g (0.2 M) of ethyl 2-oxo-2-(4-chlorophenyl)acetate are placed in 400 ml of CH2Cl2 in a 500 ml reactor. 22.8 g (0.1 M) of 2,2-diphenylpropane-1,3-diol and then 14.2 g (0.1 M) of BF3.Et2O are added. The mixture is left to react with stirring for 72 h at room temperature. The reaction mixture is taken up in NaHCO3 solution. The organic phase is washed with saturated NaCl solution. After drying over Na2SO4 and concentration, a very thick oil is obtained. 150 ml of isopropyl ether are added and a white precipitate forms. After filtration, 30 g of product melting at 156-158° C. are obtained (yield: 71%).

Workup

  1. waitThe mixture is left
  2. customto react
  3. washThe organic phase is washed with saturated NaCl solution
  4. dry with materialAfter drying over Na2SO4 and concentration
  5. customa very thick oil is obtained
  6. filtrationAfter filtration, 30 g of product melting at 156-158° C.
  7. customare obtained (yield: 71%)

Sources & evidence

ORD record
ord-2169fac0a9014699bb9176b535bf9222
Source dataset
uspto-grants-2003_03
Patent number
US06528538B1

Reaction notes

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