Ethylene Glycol → HCID 18924616, compound

HRID 2256968Notes

Reaction equation

HRID 2256968 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-056b02b8dd74437abfc024d58f3d5857
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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