Toluene → HCID 86753272, compound

HRID 355322Notes

Reaction equation

HRID 355322 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH:14]=[CH:13]1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.[C:30]1(C)[CH:35]=CC=C[CH:31]=1>>[C:15]([O:17][CH2:31][CH2:30][CH2:35][CH2:29][CH2:19][CH2:24][CH2:23][CH2:22][CH:21]=[CH2:20])(=[O:16])/[CH:14]=[CH:13]\[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10])=[O:18]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7923Maleic AnhydrideHCID 256129-Decen-1-ol

Product 1

HCID 86753272HCID 86753272, compound

Procedure

9-Decen-1-ol (Rosalva) in the amount of 50.00 g (0.320 mol) and maleic anhydride in the amount of 12.55 g (0.128 mol), toluene in the amount of 200 ml, and p-toluenesulfonic acid in the amount of 1.24 g (6.40 mmol) were combined in a flask fitted with a condenser, Dean-Stark trap, and argon inlet. The mixture was heated to reflux for 18 h. The cooled mixture was concentrated by rotary evaporation and then stripped by Kugelrohr distillation to remove excess alcohol. Purity of the product was determined by thin layer chromatography and the structure confirmed by 1H and 13C NMR.

Workup

  1. customfitted with a condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 18 h
  4. concentrationThe cooled mixture was concentrated by rotary evaporation
  5. distillationstripped by Kugelrohr distillation
  6. customto remove excess alcohol

Sources & evidence

ORD record
ord-ae8ddf0e4bbe40c6be64f22f15a190ee
Source dataset
uspto-grants-1998_11
Patent number
US05830835

Reaction notes

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