Boron trifluoride etherate → 2-[4-(4-Chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one

HRID 1702539Notes

Reaction equation

HRID 1702539 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.O[C:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:21][CH3:22])[C:18]([OH:20])=[O:19].B(F)(F)F.CCOCC>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]3[O:20][C:18](=[O:19])[C:17]([CH2:21][CH3:22])([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:13]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 2873222-Hydroxy-2-phenylbutanoic acidHCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 127737622-[4-(4-Chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-oneYield 45%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 4-(4-chlorophenyl)benzaldehyde (2.16 g.) and 2-hydroxy-2-phenylbutyric acid (1.8 g.) in anhydrous diethyl ether (50 ml.) was added boron trifluoride etherate (2.2 g.). After stirring at room temperature for 12 hours, the solution was washed with 10% w/v sodium acetate solution (2×20 ml.) and then with water (2×20 ml.) and dried (Na2SO4). The solution was filtered and evaporated to give an oil which on crystallisation from methanol gave 2-[4-(4-chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one (1.7 g.) m.p. 80°-83° C.

Workup

  1. washthe solution was washed with 10% w/v sodium acetate solution (2×20 ml.)
  2. dry with materialwith water (2×20 ml.) and dried (Na2SO4)
  3. filtrationThe solution was filtered
  4. customevaporated
  5. customto give an oil which
  6. customon crystallisation from methanol

Sources & evidence

ORD record
ord-1041ae49bc89418596993a2520478c20
Source dataset
uspto-grants-1982_09
Patent number
US04348322

Reaction notes

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