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

HRID 1716791Notes

Reaction equation

HRID 1716791 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]>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

4

Reactant 2

HCID 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 with a water trap for 2 h. After cooling, the reaction mixture was filtered, washed twice with water and then concentrated under reduced pressure. The remaining oil was mixed with heptane, whereupon the product precipitates and was filtered off and washed with heptane. Yield: 57.3 g (68% of theory). MS (API-ES, pos) m/z=301, 303 [M+H]+

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux with a water trap for 2 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. washwashed twice with water
  6. concentrationconcentrated under reduced pressure
  7. additionThe remaining oil was mixed with heptane, whereupon the product
  8. customprecipitates
  9. filtrationwas filtered off
  10. washwashed with heptane

Sources & evidence

ORD record
ord-af87ffe8e9e342969c196805bfe1e7a0
Source dataset
uspto-grants-2010_09
Patent number
US07803834B2

Reaction notes

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