Ammonium Chloride → 3-(1,3-Dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propanol

HRID 1058157Notes

Reaction equation

HRID 1058157 reaction equation
Br[CH2:2][CH2:3][CH:4]1[O:9][CH2:8][CH2:7][CH2:6][O:5]1.[CH:10]12[CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1>[O:5]1[CH2:6][CH2:7][CH2:8][O:9][CH:4]1[CH2:3][CH2:2][CH:17]([CH:11]1[CH2:12][CH:13]2[CH2:16][CH:10]1[CH:15]=[CH:14]2)[OH:18]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-

Product 1

HCID 222810373-(1,3-Dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propanolYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A Grignard reagent was customarily prepared from 36.2 g of 2-(2-bromoethyl)-1,3-dioxane in 200 ml of dry tetrahydrofuran. Then 19.5 g of 5-norbornene-2-carbaldehyde was added dropwise over 30 minutes to the Grignard reagent at 20° C. Stirring was continued for 30 minutes whereupon the reaction solution was added to a saturated aqueous solution of ammonium chloride to stop reaction. After diethyl ether extraction, the organic layer was successively washed with water, saturated sodium bicarbonate water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 36.2 g of 3-(1,3-dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propanol (boiling point 125° C./27 Pa, yield 95%).

Workup

  1. customreaction
  2. extractionAfter diethyl ether extraction
  3. washthe organic layer was successively washed with water, saturated sodium bicarbonate water and saturated sodium chloride water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuum
  6. distillationIt was further purified by vacuum distillation

Sources & evidence

ORD record
ord-c5af1ee39f0a4ad480d1ebb7c1e15356
Source dataset
uspto-grants-2003_02
Patent number
US06515149B2

Reaction notes

Loading…