Ethylene Glycol → HCID 18924616, compound

HRID 266582Notes

Reaction equation

HRID 266582 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]1[O:13][CH2:12][CH2:11][O:5]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 678472-Chloro-6-fluorobenzaldehyde

Product 1

HCID 18924616HCID 18924616, compoundYield 116.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloro-6-fluorobenzaldehyde (100 g), ethylene glycol (192 g) and p-toluenesulphonic acid (17 g) were dissolved in toluene and heated under reflux for four days using a Dean and Stark adapter to collect the water. After cooling the mixture was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness yielding 2-(2-chloro-6-fluorophenyl)-1,3-dioxolane (149 g) as an orange oil, NMR (CDCl3) 4.05(m,2H), 4.3(m,2H), 6.35(s, 1H), 7.2(m,3H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for four days
  3. customto collect the water
  4. temperatureAfter cooling the mixture
  5. washwas washed with water
  6. dry with materialdried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-514f4e934a9e40ca83a48cb738c5272f
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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