Triethylamine → 2,2-Dimethyl-4-((phenylmethoxy)methyl)-1,3-dioxolane

HRID 1955360Notes

Reaction equation

HRID 1955360 reaction equation
C1OC1CO.C(N(CC)CC)C.[CH2:13]([O:20][CH2:21][CH:22]1[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24]C1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C1C=CC=CC=1>[CH2:13]([O:20][CH2:21][CH:22]1[CH2:27][O:26][C:25]([CH3:28])([CH3:29])[O:24]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 11164GlycidolHCID 23295265HCID 23295265, compound

Product 1

HCID 857952,2-Dimethyl-4-((phenylmethoxy)methyl)-1,3-dioxolaneYield 81%

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Conditions

Temperature
25 °C

Procedure

Boron trifluoride-diethyl ether complex (0,9 ml,0.007 ml) was dropped in benzyl alcohol (92 ml) of glycidol (22.01 g, 0.3 mol) on ice bath. After dropping the mixture was stirred for 8 hours at 25° C. After the reaction was over, triethylamine was added thereto and benzyl alcohol was removed in vacuo. The desidue was dissolved in acetone and thereto p-toluenesulfonic acid was added. The mixture was reacted for 8 hours at 25° C. After the completion of the reaction triethylamine was added thereto and acetone was removed in vacuo. The crude product was distilled to give a mixture (43.8 g, yield 81%) of 4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane and 5-benzyloxymethyl-2,2-dimethyl-1,3-dioxane. The ratio of the dioxolane and the dioxane was 8 to 1 by analysis with gas chromatography.

Workup

  1. additionwas added
  2. custombenzyl alcohol was removed in vacuo
  3. dissolutionThe desidue was dissolved in acetone
  4. additionp-toluenesulfonic acid was added
  5. customThe mixture was reacted for 8 hours at 25° C
  6. additionwas added
  7. customacetone was removed in vacuo
  8. distillationThe crude product was distilled

Sources & evidence

ORD record
ord-5db26eb5d96c4028806a6d5df2d0412e
Source dataset
uspto-grants-2000_09
Patent number
US06124479

Reaction notes

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