Lactic Acid → 2-(4-Chlorophenoxymethyl)-5-methyl-1,3-dioxolan-4-one

HRID 329131

Reaktionsgleichung

Reaktionsgleichung von HRID 329131
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH:8]=[O:9])=[CH:4][CH:3]=1.[C:12]([OH:17])(=[O:16])[CH:13]([CH3:15])O.B(F)(F)F.CCOCC>CCOCC.O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH:8]2[O:17][C:12](=[O:16])[CH:13]([CH3:15])[O:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 612Lactic AcidHCID 8000Boron trifluoride etherateHCID 114806982-(4-Chlorophenoxy)acetaldehyde

Produkt 1

HCID 123799602-(4-Chlorophenoxymethyl)-5-methyl-1,3-dioxolan-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 17.05g (0.07 mole) of 4-chlorophenoxyacetaldehyde in 100 ml of ether was added 9.0g (0.1 mole) of lactic acid dissolved in 50 ml of tetrahydrofuran. To the clear solution was added 15 g (0.105 mole) of boron trifluoride etherate. After 24 hours at ambient temperature, the reaction mixture was washed with aqueous sodium bicarbonate, dried, concentrated, and purified by silica chromatography. The first fraction that emerged from the column was 2-(4-chlorophenoxymethyl-10-5-methyl-1,3-dioxolan-4-one, the transisomer, having a melting point of 37-40°. The second fraction was the cis isomer which melted at 53°-55°.

Aufarbeitung

  1. washthe reaction mixture was washed with aqueous sodium bicarbonate
  2. customdried
  3. concentrationconcentrated
  4. custompurified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-69e5865e7f024734930c831bf68c4df1
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04019892

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