Ethylene Glycol → 2-(2-Acetoxyphenyl)-1,3-dioxolan

HRID 1649110Notes

Reaction equation

HRID 1649110 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2].[CH2:13](O)[CH2:14][OH:15].O>C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]1[O:15][CH2:14][CH2:13][O:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 2372282-Formylphenyl acetate

Product 1

HCID 155835892-(2-Acetoxyphenyl)-1,3-dioxolan

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Hydroxygenzaldehyde (10 g) was dissolved in acetic anhydride (30 ml) and pyridine (30 ml) followed by stirring at room temperature for 3 hours. The reaction mixture was poured into ice-water and the resulting precipitate was recovered by filtration. The precipitate was dissolved in chloroform (100 ml), washed with water, dried and evaporated to give 2-acetoxybenzaldehyde. To a solution of 2-acetoxy-benzaldehyde (13 g) and ethyleneglycol (10 ml) in benzene (80 ml) was added Amberlist 15 (Rohm and Haas Co.) (3 g) and followed by refluxing for 5 hours. Water generated during refluxing was removed as an azeotropic mixture. The reaction mixture was washed with an aqueous solution of sodium bicarbonate, and then with water, and dried and evaporated. The residue was distilled under reduced pressure to collect a fraction distilled out at 115°-125° C./4 mmHg to give 10 g of 2-(2-acetoxyphenyl)-1,3-dioxolan. To a solution of 2-(2-acetoxy-phenyl)-1,3-dioxolan (19.6 g) in dichloromethane (50 ml), bis(trimethylsilyl)-5-fluorouracil prepared as in Example 1 from 5-fluorouracil (10 g) was added and treated as in Example 10 to give 4.2 g of crystalline 1-[α-(2-hydroxyethoxy)-2-acetoxybenzyl]-5-fluorouracil.

Workup

  1. temperatureby refluxing for 5 hours
  2. temperatureduring refluxing
  3. customwas removed as an azeotropic mixture
  4. washThe reaction mixture was washed with an aqueous solution of sodium bicarbonate
  5. dry with materialwith water, and dried
  6. customevaporated
  7. distillationThe residue was distilled under reduced pressure
  8. customto collect a fraction
  9. distillationdistilled out at 115°-125° C./4 mmHg

Sources & evidence

ORD record
ord-d5b70c05cdb74ae3abf8e0ef4c0a662c
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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