Ethylene Glycol → Benzyl oximino-acetoacetate ethylene ketal

HRID 596908Notes

Reaction equation

HRID 596908 reaction equation
O.[N:2](=[CH:4][C:5](=[O:17])[CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[OH:3].[CH2:18](O)[CH2:19][OH:20].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1>[CH2:19]1[O:20][C:5]([CH:4]=[N:2][OH:3])([CH2:6][C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[O:17][CH2:18]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 69252-Methylbenzenesulfonic acidHCID 86734531HCID 86734531, compound2×

Product 1

HCID 86734545Benzyl oximino-acetoacetate ethylene ketalYield 35%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a two liter flask fitted with a Dean Stark water separator and a condenser were placed 186.5 g. (0.85 mole) of benzyl oximino-acetoacetate (17), 62 g. (1 mole) of ethylene glycol, 800 ml. of benzene (reagent grade) and 2 g. of toluenesulfonic acid. The reaction mixture was boiled at reflux until 15 ml. of water was removed (3 hours). The benzene solution was washed once with saturated sodium bicarbonate solution and once with brine. After drying over anhydrous sodium sulfate, the benzene solution was evaporated, leaving 212 g. (94%) of 17 as a light yellow oil. Its NMR spectrum was consistent with the assigned structure. Generally the compound was used as such in subsequent reaction but one of the isomers can be crystallized in 35% yield from toluene-petroleum ether, m.p. 52° C. ##STR154##

Workup

  1. temperatureat reflux until 15 ml
  2. customof water was removed (3 hours)
  3. washThe benzene solution was washed once with saturated sodium bicarbonate solution and once with brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe benzene solution was evaporated
  6. customleaving 212 g
  7. customsuch in subsequent reaction but one of the isomers
  8. customcan be crystallized in 35% yield from toluene-petroleum ether, m.p. 52° C.

Sources & evidence

ORD record
ord-44191a7365fe418a8651b810919af31f
Source dataset
uspto-grants-1977_03
Patent number
US04012383

Reaction notes

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