Ethylene Glycol → Methyl 4-[(2-methyl-1,3-dioxolan-2-yl)methyl]benzoate

HRID 434366Notes

Reaction equation

HRID 434366 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[CH2:15](O)[CH2:16][OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:16]1[O:17][C:12]([CH3:13])([CH2:11][C:8]2[CH:9]=[CH:10][C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:6][CH:7]=2)[O:14][CH2:15]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 11137970Methyl 4-(2-oxopropyl)benzoate

Product 1

HCID 56629009Methyl 4-[(2-methyl-1,3-dioxolan-2-yl)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(4-carbomethoxyphenyl)propan-2-one (17.3 g), ethan-1,2-diol (5.6 g) and p-toluenesulphonic acid (200 ml) in benzene (150 ml) was refluxed under a Dean and Stark head until the theoretical amount of water had been collected (ca. 4 hours). The solvent was evaporated and the residue was partitioned between sodium bicarbonate solution and ether. The ethereal extract was washed with water, dried, evaporated and distilled to give 15.7 g (74%), bp 136-140/1.5 mm.

Workup

  1. customhad been collected (ca. 4 hours)
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between sodium bicarbonate solution and ether
  4. extractionThe ethereal extract
  5. washwas washed with water
  6. customdried
  7. customevaporated
  8. distillationdistilled
  9. customto give 15.7 g (74%), bp 136-140/1.5 mm

Sources & evidence

ORD record
ord-8ddc3f88f3b846edb9af76d3c388f4d8
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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