Neopentyl glycol → 2-(4-Bromophenyl)-2-(3-chloropropyl)-5,5-dimethyl-1,3-dioxane

HRID 747710Notes

Reaction equation

HRID 747710 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1.[CH3:14][C:15]([CH3:20])([CH2:18]O)[CH2:16][OH:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:9][CH2:10][CH2:11][Cl:12])[O:17][CH2:16][C:15]([CH3:20])([CH3:18])[CH2:14][O:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 31344Neopentyl glycolHCID 783174'-Bromo-4-chlorobutyrophenoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 126147752-(4-Bromophenyl)-2-(3-chloropropyl)-5,5-dimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 g (38.2 mmol) of 4′-bromo-4-chlorobutyrophenone, 4 g (38.2 mmol) of 2,2-dimethyl-1,3-propanediol and 200 mg (1 mmol) of p-toluenesulfonic acid monohydrate were heated under reflex in benzene for 3 days to conduct the azeotropic dehydration. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. After the extraction with ethyl acetate, the extract was washed with water and saturated aqueous common salt solution and then dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. washthe extract was washed with water and saturated aqueous common salt solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-01cf6374aaa0467c886a41fd7ca1e808
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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