Water → 4-Methyl-2-(4,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-dioxolan

HRID 566856Notes

Reaction equation

HRID 566856 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]([CH:10]=[O:11])=[CH:4][CH2:3]1.[CH2:12]([OH:16])[CH:13](O)[CH3:14].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:14][CH:13]1[CH2:12][O:16][CH:10]([C:5]2[C:6]([CH3:8])([CH3:9])[CH2:7][CH:2]([CH3:1])[CH2:3][CH:4]=2)[O:11]1

Participants

6

Reactant 3

HCID 962WaterHCID 1030Propylene GlycolHCID 212637424,6,6-Trimethylcyclohex-1-ene-1-carbaldehyde

Product 1

HCID 212637524-Methyl-2-(4,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-dioxolanYield 65.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

4,6,6-Trimethyl-1-cyclohexen-1-carbaldehyde (2 g, 13 mmole), 1,2-propanediol (4 g, 53 mmole) and p-toluenesulfonic acid (50 mg) were refluxed in 20 ml of toluene, with water separation in a Dean-Stark apparatus, during 6 h. The resulting solution was washed with a NaHCO3 solution and the crude product distilled at a bath temperature of 80°/0.5 hPa, to obtain 1.78 g of the desired product in the form of a mixture of isomers.

Workup

  1. washThe resulting solution was washed with a NaHCO3 solution
  2. distillationthe crude product distilled at a bath temperature of 80°/0.5 hPa

Sources & evidence

ORD record
ord-6470f5e3c117442d98ad52d6a8e38a77
Source dataset
uspto-grants-2001_01
Patent number
US06177400B1

Reaction notes

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