Ethylene Glycol → Dimethyl(3-(2-tetrahydropyranyl)oxy-2-oxoheptyl)phosphonate

HRID 1386457Notes

Reaction equation

HRID 1386457 reaction equation
[CH3:1][O:2][P:3]([CH2:7][C:8](=[O:18])[C:9](C)(C)[CH2:10][CH2:11][CH2:12][CH2:13]OC)(=[O:6])[O:4][CH3:5].[CH2:19]([OH:22])[CH2:20]O.[C:23]1(C)[CH:28]=CC(S(O)(=O)=O)=C[CH:24]=1.[OH2:34]>C1(C)C=CC=CC=1>[CH3:5][O:4][P:3]([CH2:7][C:8](=[O:18])[CH:9]([O:34][CH:19]1[CH2:20][CH2:28][CH2:23][CH2:24][O:22]1)[CH2:10][CH2:11][CH2:12][CH3:13])(=[O:6])[O:2][CH3:1]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 15223961Dimethyl (7-methoxy-3,3-dimethyl-2-oxoheptyl)phosphonate

Product 1

HCID 54345769Dimethyl(3-(2-tetrahydropyranyl)oxy-2-oxoheptyl)phosphonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The ketone (4) (1.95 g) was dissolved in toluene (150 ml), and ethylene glycol and p-toluenesulfonic acid (catalytic amount) were added. The solution was heated under reflux overnight while water produced was distilled off. After the usual work-up, ketal (5) was obtained. Yield: 1.8 g (84%).

Workup

  1. temperatureThe solution was heated
  2. customproduced
  3. distillationwas distilled off

Sources & evidence

ORD record
ord-84e5251457064220a28c0fe2168342e9
Source dataset
uspto-grants-2001_07
Patent number
US06265440B1

Reaction notes

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