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

HRID 2070542Notes

Reaction equation

HRID 2070542 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH2:15][C:13](=[O:14])[O:12]1>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:15]2[C:16](=[O:17])[O:18][C:11]([CH3:19])([CH3:10])[O:12][C:13]2=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 3705415-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 66.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

To a suspension of 4-hydroxybenzaldehyde (35 g) in water (300 mL) heated up to 75° C. was added a suspension of Meldrum's acid (43.4 g) in water (300 mL), followed by stirring the reaction mixture successively at 75° C. for 8.5 hours, at room temperature for 14 hours and under ice-cooling for 2 hours. The resulting crystal was filtered, washed with ice-cold water and dried in vacuo to give 5-(4-hydroxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (47.3 g).

Workup

  1. additionwas added
  2. waitat room temperature for 14 hours
  3. temperatureunder ice-cooling for 2 hours
  4. filtrationThe resulting crystal was filtered
  5. washwashed with ice-cold water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-db0fb5addd5c4522bb120c6f2d26bc3f
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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