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

HRID 507742Notes

Reaction equation

HRID 507742 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH:10][CH2:11][C:12]([CH3:16])([CH2:14]O)[CH3:13]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:10][CH2:11][C:12]([CH3:16])([CH3:14])[CH2:13][O:7]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31344Neopentyl glycolHCID 707414-Bromobenzaldehyde

Product 1

HCID 137145152-(4-Bromophenyl)-5,5-dimethyl-1,3-dioxaneYield 93%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent2×

Procedure

A mixture of 4-bromobenzaldehyde (100 g, 0.54 mole), neopentyl glycol (115 g, 1.10 mole), and p-toluenesulfonic acid (800 mg, 4 mmole) in benzene (800 mL) was heated to reflux using a Dean Stark apparatus for 16 h. The reaction mixture was cooled to room temperature and most of the benzene was removed. The residue was partitioned between ethyl acetate (500 mL) and cold water (150 mL). The organic phase was washed with water (2×150 mL) and brine (1×150 mL), then dried (Na2SO4) and concentrated to give the desired product (136 g, 93%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customfor 16 h
  4. customwas removed
  5. customThe residue was partitioned between ethyl acetate (500 mL) and cold water (150 mL)
  6. washThe organic phase was washed with water (2×150 mL) and brine (1×150 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1146809866274295b6e3a0bb7a28a812
Source dataset
uspto-grants-2010_08
Patent number
US07786112B2

Reaction notes

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