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

HRID 390385

Reaction equation

HRID 390385 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-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-hydroxybenzaldehyde (20 g, 163 mmol) in water (250 mL) is added Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) (24.78 g, 171 mmol) as a slurry in water (250 mL) at 75° C. The reaction mixture is agitated for 2 hours, cooled in an ice bath, and extracted with EtOAc (2×400 mL). The combined extracts are washed with saturated brine, dried over sodium sulfate, filtered, and concentrated to a yellow solid (39 g, 97%). ESI/MS m/z 247.1 (M−H)−.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with EtOAc (2×400 mL)
  3. washThe combined extracts are washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow solid (39 g, 97%)

Sources & evidence

ORD record
ord-0b6a76412b7d4af8ac7993cb8fbb8a5b
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Linked notes

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