3-Hydroxybenzaldehyde → 5-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1662368Notes

Reaction equation

HRID 1662368 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O>O>[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[C:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9]

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 6053805-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

2,2-Dimethyl-1,3-dioxane-4,6-dione 66.6Q (available from Aldrich) (28.8 g, 200 mmol) was added to a mixture of 3-hydroxybenzaldehyde 66.6R (available from Aldrich) (24.4 g, 200 mmol) in water (1000 mL) at 85° C. The resulting mixture was stirred at 85° C. for 2 hours. The reaction was allowed to cool and then filtered to provide 5-(3-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 66.6S (41.4 g, 83% yield) as a yellow solid.

Workup

  1. temperatureto cool
  2. filtrationfiltered

Sources & evidence

ORD record
ord-e4c43ce002f340c398ad09be1dd57635
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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