Diethyl Ether → 3-(1,3-Dioxolan-2-YL)benzophenone

HRID 2164434Notes

Reaction equation

HRID 2164434 reaction equation
[C:1]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1C=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[Si](OC)(OC)[O:20][CH2:21][CH2:22][O:23][Si](OC)(OC)OC.[C:35]([O-])(O)=O.[Na+].C(OCC)C>ClCCl.FC(F)(F)S(OC[Si](C)(C)C)(=O)=O.N1C=CC=CC=1>[C:1]([C:2]1[CH:3]=[C:4]([CH:35]2[O:20][CH2:21][CH2:22][O:23]2)[CH:5]=[CH:6][CH:7]=1)(=[O:8])[C:9]1[CH:10]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 1611952-BenzoylbenzaldehydeHCID 516892Sodium BicarbonateHCID 13195968HCID 13195968, compound

Product 1

HCID 105150883-(1,3-Dioxolan-2-YL)benzophenone

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 2760857(Trimethylsilyl)methyl Trifluoromethanesulfonate [Trimethylsilylmethylating Reagent]CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of benzoylbenzaldehyde (2 g, 10 mmol) and 1,2-bis-(trimethoxysiloxy)ethane (2.3 g, 11 mmol) in dry dichloromethane (30 cm3) under N2 at room temperature was added trimethylsilylmethyl trifluoromethanesulphonate (5 drops). After stirring at 20° C. for 48 hours, pyridine (3 drops) was added followed by saturated NaHCO3 (20 cm3) and diethyl ether (20 cm3). The resulting mixture was stirred for 30 minutes. The ethereal layer was separated off and the aqueous layer extracted twice more with diethyl ether. The combined extracts were washed with water, dried over a mixture of anhydrous Na2CO3 and anhydrous Na2SO4 (1:1) and the solvent removed in vacuo to give 2-(3-benzoylphenyl)-1,3-dioxolane, nD20 1.5890. Yield 2.2 g (91.7%).

Workup

  1. stirringThe resulting mixture was stirred for 30 minutes
  2. customThe ethereal layer was separated off
  3. extractionthe aqueous layer extracted twice more with diethyl ether
  4. washThe combined extracts were washed with water
  5. dry with materialdried over a mixture of anhydrous Na2CO3 and anhydrous Na2SO4 (1:1)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2ae659d81b1c46e0943d7a38d3145739
Source dataset
uspto-grants-1985_03
Patent number
US04504491

Reaction notes

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