Hydrochloric Acid → 8-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane

HRID 1401756Notes

Reaction equation

HRID 1401756 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C1COCC1>[CH2:15]([O:14][CH2:13][CH:10]1[CH2:11][CH2:12][C:7]2([O:6][CH2:5][CH2:4][O:3]2)[CH2:8][CH2:9]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Product 1

HCID 103780318-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decaneYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 1.32 g (33 mmol) of 60% NaH was added to a solution containing 5.2 g (30 mmol) of 1,4-dioxaspiro[4,5]decan-8-ylmethanol dissolved in 75 ml of THF. After stirring for 10 minutes, benzyl bromide (50 mmol) was added and the mixture was stirred for 18 hours at room temperature. Then, the reaction solution was neutralized with 1N aqueous hydrochloric acid solution, and concentrated under reduced pressure. The residue was dissolved in ether, washed twice with water and once with brine, and the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography to obtain 8-(benzyloxymethyl)-1,4-dioxaspiro[4,5]decane (6.0 g, 77%) as a colorless clear oil.

Workup

  1. stirringthe mixture was stirred for 18 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. washwashed twice with water and once with brine
  5. customthe solvent was evaporated under reduced pressure
  6. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7f0e29f1249544ee9e2ba44964b075f3
Source dataset
uspto-grants-2014_12
Patent number
US08907128B2

Reaction notes

Loading…