Ethylene carbonate → HCID 54070148, compound

HRID 1462963Notes

Reaction equation

HRID 1462963 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]2)=[CH:4][CH:3]=1.C1(=O)O[CH2:21][CH2:20][O:19]1.[OH-].[Na+]>[I-].C[N+](C)(C)C.O.C(O)C>[OH:19][CH2:20][CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]2)=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 7303Ethylene carbonateHCID 14798Sodium HydroxideHCID 20452436HCID 20452436, compound

Product 1

HCID 54070148HCID 54070148, compoundYield 44.4%

Reagents, catalysts & solvents 3

HCID 638175-58-1CatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4'-Hydroxyflavan (2.26 g.), ethylene carbonate (8.8 g.) and tetramethylammonium iodide (0.30 g.) were heated together at 140° C. for 4 hrs. Sodium hydroxide (6.5 g) in water (20 ml.) and ethanol (250 ml.) was added, and the solution boiled under reflux for 5 hrs. The solution was filtered, diluted with water, and extracted 3 times with ether. The combined extracts were dried and evaporated, and the residue chromatographed on neutral alumina. The product was eluted with chloroform and after evaporation of the solvent was recrystallised from 60°-80° C. petroleum ether to yield 4'-(2-hydroxyethoxy) flavan (1.2 g.) m.p. 84°-85° C.

Workup

  1. temperatureunder reflux for 5 hrs
  2. filtrationThe solution was filtered
  3. additiondiluted with water
  4. extractionextracted 3 times with ether
  5. customThe combined extracts were dried
  6. customevaporated
  7. customthe residue chromatographed on neutral alumina
  8. washThe product was eluted with chloroform
  9. customafter evaporation of the solvent
  10. customwas recrystallised from 60°-80° C. petroleum ether

Sources & evidence

ORD record
ord-dc877b95a8d846108d00e26e8105f184
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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