Ethylene Glycol → HCID 18431469, compound

HRID 1278929Notes

Reaction equation

HRID 1278929 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([O:19][CH3:20])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:21](O)[CH2:22][OH:23].CC1C=CC(S(O)(=O)=O)=CC=1>CC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([O:19][CH3:20])[CH:11]=3)[O:23][CH2:22][CH2:21][O:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 18431481HCID 18431481, compound

Product 1

HCID 18431469HCID 18431469, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (4-chlorophenyl)(3-methoxy-4-nitrophenyl)methanone (40.7 g), 1,2-ethanediol (31.2 ml) and 4-methylbenzene sulfonic acid (5.31 g) in methylbenzene (320 ml) was stirred and refluxed using a Dean-Stark apparatus. The mixture was washed with K2CO3 (10%) and extracted with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 22.48 g (50.4%) of 2-(4-chlorophenyl)-2-(3-methoxy-4-nitrophenyl)-1,3-dioxolane (interm. 39).

Workup

  1. temperaturerefluxed
  2. washThe mixture was washed with K2CO3 (10%)
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from DIPE
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-ecc940586ee647ea9f8e5e83acd8637a
Source dataset
uspto-grants-2002_09
Patent number
US06444812B1

Reaction notes

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