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

HRID 372339Notes

Reaction equation

HRID 372339 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 2.5g (0.033 mole) of glycolic acid, 4.2g (0.025 mole) of 4-chloro-2-methylphenoxyacetaldehyde and 10g (0.07 mole) of 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 3.8g 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-970614a4618c4c47a14462efc5ea1cc7
Source dataset
uspto-grants-1978_05
Patent number
US04090861

Reaction notes

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