Glycolic Acid → 2-(4-Chloro-2-methylphenoxymethyl)-1,3-dioxolan-4-one

HRID 461281Notes

Reaction equation

HRID 461281 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2]O.[Cl:6][C:7]1[CH:16]=[CH:15][C:10]([O:11][CH2:12][CH:13]=[O:14])=[C:9]([CH3:17])[CH:8]=1.B(F)(F)F.CCOCC>CCOCC.O1CCCC1>[Cl:6][C:7]1[CH:16]=[CH:15][C:10]([O:11][CH2:12][CH:13]2[O:5][C:1](=[O:4])[CH2:2][O:14]2)=[C:9]([CH3:17])[CH:8]=1

Participants

6

Reactant 3

HCID 757Glycolic AcidHCID 8000Boron trifluoride etherateHCID 123914592-(4-Chloro-2-methylphenoxy)acetaldehyde

Product 1

HCID 203271852-(4-Chloro-2-methylphenoxymethyl)-1,3-dioxolan-4-oneYield 62.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 2.5 g (0.033 mole) of glycolic acid, 4.1 g (0.025 mole) of 4-chloro-2-methylphenoxyacetaldehyde and 10 g (0.07 mole) or boron trifluoride etherate in 50 ml of ether and 30 ml of tetrahydrofuran was allowed to stand at room temperature for 24 hours. The dark solution was washed with aqueous sodium bicarbonate, dried and concentrated to dryness. Recrystallization from ether - hexane gave 3.8 g of 2-(4-chloro-2-methylphenoxymethyl)-1,3-dioxolan-4-one having a melting point of 42°-44°.

Workup

  1. washThe dark solution was washed with aqueous sodium bicarbonate
  2. customdried
  3. concentrationconcentrated to dryness
  4. customRecrystallization from ether - hexane

Sources & evidence

ORD record
ord-f006f8c2887846b0928e29fcbe939c97
Source dataset
uspto-grants-1977_12
Patent number
US04062670

Reaction notes

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