Epichlorohydrin → 1,4-Dioxaspiro(4.5)decane

HRID 1290973Notes

Reaction equation

HRID 1290973 reaction equation
O=C1[C:6]2([CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)C(=O)CC1.C(C(C)CC1CC(CC2C=C[C:28]([O:31]C)=[CH:27]C=2)CCC1=O)#N.[Br-].COC1C=CC(C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(C1OC1)Cl>C1(C)C=CC=CC=1>[O:12]1[C:9]2([CH2:8][CH2:7][CH2:6][CH2:11][CH2:10]2)[O:31][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 2734885(4-Methoxybenzyl)(triphenyl)phosphonium bromideHCID 189197142-(2-Cyanopropyl)-4-(4-methoxybenzyl)cyclohexanone 1,4-Dioxospiro[4,5]decan-8-one

Product 1

HCID 90931,4-Dioxaspiro(4.5)decaneYield 136.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2-Cyanopropyl)-4-(4-methoxybenzyl)cyclohexanone 1,4-Dioxospiro[4,5]decan-8-one (45.6 g) was added to a mixture of 4-methoxybenzyl triphenylphosphonium bromide (127.3 g) and epichlorohydrin (100 ml) in toluene (1500 ml) and heated at reflux under a nitrogen atmosphere for 36 hours. The solvent was evaporated under reduced pressure and the residue was extracted into hexane. The hexane solution was evaporated under reduced pressure and the residue distilled at 24° C./1 mmHg to give 8-(4-methoxybenzylidine)- 1,4-dioxaspiro[4,5]-decane, (19 g).

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere for 36 hours
  3. customThe solvent was evaporated under reduced pressure
  4. extractionthe residue was extracted into hexane
  5. customThe hexane solution was evaporated under reduced pressure
  6. distillationthe residue distilled at 24° C./1 mmHg

Sources & evidence

ORD record
ord-e66d4edfd0d9425dab0ffcd042614356
Source dataset
uspto-grants-1998_05
Patent number
US05753676

Reaction notes

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