Water → 2-(3-Bromo-4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane

HRID 1666729Notes

Reaction equation

HRID 1666729 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[OH:12][CH2:13][C:14]([CH3:18])([CH2:16]O)[CH3:15].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:12][CH2:13][C:14]([CH3:18])([CH3:16])[CH2:15][O:6]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 31344Neopentyl glycolHCID 986623-Bromo-4-methoxybenzaldehyde

Product 1

HCID 8494352-(3-Bromo-4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Bromo-4-methoxybenzaldehyde (60.0 g, 279 mmol) was dissolved in toluene (600 mL), and after addition of neopentyl glycol (32.0 g, 306 mmol) and Amberlyst-15 (3.6 g) the reaction mixture was heated under reflux for 2 hours on a water separator. After cooling, the reaction mixture was filtered, washed twice with water, and then concentrated under reduced pressure. The oil residue was combined with heptane, and the product which precipitated was filtered off and washed with heptane.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. washwashed twice with water
  5. concentrationconcentrated under reduced pressure
  6. customthe product which precipitated
  7. filtrationwas filtered off
  8. washwashed with heptane

Sources & evidence

ORD record
ord-ed569ced8d824a729af0052a3931b2d0
Source dataset
uspto-grants-2011_10
Patent number
US08044079B2

Reaction notes

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