Toluene → HCID 66888852, compound

HRID 1733757Notes

Reaction equation

HRID 1733757 reaction equation
[CH:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH:12]=[CH:11]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.[C:28]1(C)C=CC=CC=1>O>[C:13]([O:15][CH2:28][CH2:27][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)(=[O:14])/[CH:12]=[CH:11]\[C:10]([O:9][CH2:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7923Maleic AnhydrideHCID 205082-Cyclohexylethanol

Product 1

HCID 66888852HCID 66888852, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cyclohexylethyl alcohol in the amount of 17.15 g (0.134 mol), maleic anhydride in the amount of 4.42 g (0.045 mol) and p-toluenesulfonic acid in the amount of 0.09 g (0.40 mmol) were combined with 80 mL of toluene in a flask fitted with a condenser, argon inlet and Dean-Stark trap. The mixture was heated to reflux for 18 h at which time the theoretical amount of water was collected. The product mixture was poured into separatory funnel and washed with saturated NaHCO3 solution (3×80 mL), brine (80 mL), water (80 mL), dried over MgSO4, filtered and concentrated to give an oil. The product mixture was further concentrated by Kugelrohr distillation at 85° C. (0.1 mm Hg) to give a viscous oil. 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, argon inlet
  2. temperatureThe mixture was heated
  3. customwas collected
  4. additionThe product mixture was poured into separatory funnel
  5. washwashed with saturated NaHCO3 solution (3×80 mL), brine (80 mL), water (80 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil
  10. concentrationThe product mixture was further concentrated by Kugelrohr distillation at 85° C. (0.1 mm Hg)
  11. customto give a viscous oil

Sources & evidence

ORD record
ord-fdf111aeb5a14a50a94ef17f938309ae
Source dataset
uspto-grants-1996_07
Patent number
US05531910

Reaction notes

Loading…