Benzyl Chloride → 8-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

HRID 1349380Notes

Reaction equation

HRID 1349380 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:11][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decaneYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

225 g of 1,4-dioxa-spiro[4.5]decan-8-ol were dissolved in 1100 ml of dimethyl-formamide, and 198 g of potassium tert.-butoxide were added in portions, with stirring. After one hour, 223 g of benzyl chloride were added dropwise over 30 minutes, and stirred overnight. The batch was added to 1500 ml of water/ice mixture and extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product was subjected to fractional distillation under a high vacuum. At 150° C. and a pressure of about 0.1 mbar, 294 g of 8-benzyloxy-1,4-dioxaspiro[4.5]decane were obtained.

Workup

  1. stirringstirred overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe crude product was subjected to fractional distillation under a high vacuum

Sources & evidence

ORD record
ord-c10ecef5ba9b41ae95efe0b299cb8107
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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