Toluene → HCID 69316002, compound

HRID 899036Notes

Reaction equation

HRID 899036 reaction equation
[CH3:1][C:2](=[CH:5][CH2:6][C:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:8]=1[CH3:15])[CH:3]=[O:4].[CH2:16](O)[CH2:17][CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH3:1][CH:2]([CH:3]1[O:19][CH2:18][CH2:17][CH2:16][O:4]1)[CH:5]=[CH:6][C:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:8]=1[CH3:15]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 1023752-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal

Product 1

HCID 69316002HCID 69316002, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

103 g (0.5 mol) of 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, 38 g (0.5 mol) of 1,3-propanediol and 1 g of p-toluenesulfonic acid are heated with 200 g of toluene for 2.5 hours in a water separator. After cooling, the mixture is washed with soda solution and dried over sodium sulfate. 3 g of sodium carbonate are added and the mixture is distilled on a 30 cm packed column. At 122-126° C./1.6-0.82 mbar this yields 81 g of product comprising 66% of 2-[1-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)allyl]-1,3-dioxane and also containing other isomers with double bonds.

Workup

  1. temperatureAfter cooling
  2. washthe mixture is washed with soda solution
  3. dry with materialdried over sodium sulfate
  4. addition3 g of sodium carbonate are added
  5. distillationthe mixture is distilled on a 30 cm
  6. customAt 122-126° C.
  7. additionalso containing other isomers with double bonds

Sources & evidence

ORD record
ord-be479ee4a43e4ee28bb5e1154716ed1a
Source dataset
uspto-grants-2008_04
Patent number
US07354893B2

Reaction notes

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