Mandelic Acid → 2-(2,4-Dichlorophenoxymethyl)-5-phenyl-1,3-dioxolan-4-one

HRID 372338Notes

Reaction equation

HRID 372338 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH:6]=[O:7].[C:13]([OH:23])(=[O:22])[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)O.[B]>CCOCC>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH:6]1[O:23][C:13](=[O:22])[CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:7]1

Participants

5

Reactant 3

HCID 1292Mandelic AcidHCID 50929372,4-DichlorophenoxyacetaldehydeHCID 5462311Boron

Product 1

HCID 123799682-(2,4-Dichlorophenoxymethyl)-5-phenyl-1,3-dioxolan-4-oneYield 31.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution containing 5.1g (0.025 mole) of 2,4-dichlorophenoxyacetaldehyde, 4.25g (0.028 mole) of mandelic acid, and 10.0g (0.07 mole) of boron trifluoide etherate in 250 ml of ether was allowed to stir for 2 hours at ambient temperature, washed with aqueous sodium carbonate and water, dried and concentrated. The residual solid was purified by silica chromatography to give 2.7g of 2-(2,4-dichlorophenoxymethyl)-5-phenyl-1,3-dioxolan-4-one, trans isomer, having a melting point of 68°-71°.

Workup

  1. washwashed with aqueous sodium carbonate and water
  2. customdried
  3. concentrationconcentrated
  4. customThe residual solid was purified by silica chromatography

Sources & evidence

ORD record
ord-20234b7f0e9b4999b4fc28fa4e88565c
Source dataset
uspto-grants-1978_05
Patent number
US04090861

Reaction notes

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