p-Toluenesulfonic acid → HCID 19838208, compound

HRID 476675Notes

Reaction equation

HRID 476675 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:16][CH2:17][CH3:18])=[C:5]([CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[C:10]=1[O:11][CH3:12])C=O.CC1C=CC(S(O)(=O)=O)=CC=1.CO[CH:32]([O:35][CH3:36])[O:33][CH3:34].[OH-].[K+]>CO>[CH3:12][O:11][C:10]1[C:3]([O:2][CH3:1])=[C:4]([CH2:16][CH2:17][CH3:18])[C:5]([CH:32]([O:33][CH3:34])[O:35][CH3:36])=[CH:8][C:9]=1[N+:13]([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 14797Potassium HydroxideHCID 19838283HCID 19838283, compound

Product 1

HCID 19838208HCID 19838208, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of the aldehyde from step (d) (14 g) tosic acid (0.2 g) and trimethylorthoformate (6.7 ml) in dry methanol (100 ml) was heated under reflux for 30 mins. A solution of potassium hydroxide in methanol (5 ml) was added to the reaction mixture and the solution evaporated to dryness. The residue was dissolved in ether, washed with water, dried, filtered and evaporated to leave a solid which crystallised from pentane as pale yellow prisms (11.6 g); mp 52.1°-54.0°.

Workup

  1. temperatureunder reflux for 30 mins
  2. customthe solution evaporated to dryness
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a solid which
  9. customcrystallised from pentane as pale yellow prisms (11.6 g)

Sources & evidence

ORD record
ord-6cb75f4127b04633b9a3b26b6709907a
Source dataset
uspto-grants-1989_12
Patent number
US04885313

Reaction notes

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