Sodium Bicarbonate → 5-(3-Bromobenzyl)-2,2-dimethyl-1,3-dioxane

HRID 857213Notes

Reaction equation

HRID 857213 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]([CH2:9][OH:10])[CH2:7][OH:8].O.[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1.C(=O)([O-])O.[Na+]>CC(C)=O.C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]1[CH2:7][O:8][C:15]([CH3:20])([CH3:16])[O:10][CH2:9]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 218669482-(3-Bromobenzyl)-1,3-propanediol

Product 1

HCID 218667465-(3-Bromobenzyl)-2,2-dimethyl-1,3-dioxaneYield 1,400.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

2-(3-Bromobenzyl)-1,3-propanediol (1.85 g) was dissolved in a mixture of 8 ml of acetone/18 ml of benzene, and 70 mg of p-toluenesulfonic acid monohydrate was added. The solution was subjected to azeotropic dehydration with Dean-Stark apparatus for 1 hour. After addition of saturated sodium hydrogen carbonate solution, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=4:1) to provide 1.47 g of the objective compound as colorless oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-34c24370693a42218ce877cdd688d52e
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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