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

HRID 329131Notes

Reaction equation

HRID 329131 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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°.

Workup

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

Sources & evidence

ORD record
ord-69e5865e7f024734930c831bf68c4df1
Source dataset
uspto-grants-1977_04
Patent number
US04019892

Reaction notes

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