2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 86724119, compound

HRID 1748777Notes

Reaction equation

HRID 1748777 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.[CH3:11][C:12]1([CH3:20])[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[O:13]1>O.O1CCOCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:15]2[C:16](=[O:18])[O:17][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:19])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione2×HCID 135551504-Bromo-2-methylbenzaldehyde

Product 1

HCID 86724119HCID 86724119, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-bromo-2-methylbenzaldehyde (1.99 g, 10.00 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (2.16 g, 15.0 mmol) in water (20 mL) and 1-4-dioxane (2 mL) was heated at about 75° C. for about 2 h. Additional 2,2-dimethyl-1,3-dioxane-4,6-dione (0.72 g, 5.0 mmol) was added and heating at about 75° C. was continued for about 2 h. The reaction was cooled to rt and solids were filtered off and rinsed with water (25 mL). The resulting solid was air dried on the funnel and then triturated with Et2O (about 20 mL) and filtered. The product was dried overnight in the vacuum oven at about 50° C. to yield 5-(4-bromo-2-methylbenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.75 g, 8.46 mmol, 85%) as a pale yellow solid: LC-MS (Table 1, Method g) Rt=2.43 min, m/z 341/343 (M−H+NH3)−; 1H NMR (400 MHz, DMSO-d6) δ 8.49 (s, 1H), 7.58 (d, J=1.8 Hz, 1H), 7.51-7.42 (m, 2H), 2.33 (s, 3H), 1.77 (s, 6H).

Workup

  1. temperatureheating at about 75° C.
  2. temperatureThe reaction was cooled to rt
  3. filtrationsolids were filtered off
  4. washrinsed with water (25 mL)
  5. customdried on the funnel
  6. customtriturated with Et2O (about 20 mL)
  7. filtrationfiltered
  8. customThe product was dried overnight in the vacuum oven at about 50° C.

Sources & evidence

ORD record
ord-090bd29de07749fcac3b1133f79db837
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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