Ethylene Glycol → HCID 59408350, compound

HRID 2389210Notes

Reaction equation

HRID 2389210 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]3[CH2:16][CH2:15][C:14]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH3:26])=[CH:20][CH:19]=4)(O)[CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)CO>C1(C)C=CC=CC=1>[CH2:24]([C:21]1[CH:20]=[CH:19][C:18]([C:14]2[CH2:15][CH2:16][CH:11]([CH:8]3[CH2:7][CH2:6][C:5]4([O:1][CH2:2][CH2:3][O:4]4)[CH2:10][CH2:9]3)[CH2:12][CH:13]=2)=[CH:23][CH:22]=1)[CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 59408361HCID 59408361, compound

Product 1

HCID 59408350HCID 59408350, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

250 g (about 0.7 mol) of crude 4-(1,4-dioxaspiro[4.5]dec-8-yl)-1-(4-propylphenyl)cyclohexanol are heated on a water separator together with 13.2 g (69 mmol) of p-toluenesulfonic acid monohydrate and 40.7 ml (0.73 mol) of ethylene glycol in 800 ml of toluene. The solution is washed a number of times with water and dried using sodium sulfate. The crude product remaining after removal of the solvent is purified by chromatography (SiO2, n-heptane:MTBE=5:1). 8-[4-(4-Propylphenyl)cyclohex-3-enyl]-1,4-dioxaspiro[4.5]decane is obtained as a colourless solid.

Workup

  1. washThe solution is washed a number of times with water
  2. customdried
  3. customafter removal of the solvent
  4. customis purified by chromatography (SiO2, n-heptane:MTBE=5:1)

Sources & evidence

ORD record
ord-f56ca8516f594d02bbdc2e8d360c2fd0
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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