Ethyl Acetate → HCID 22633147, compound

HRID 2417385Notes

Reaction equation

HRID 2417385 reaction equation
[C:1]([O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:15][CH3:16])(=[O:3])[CH3:2].[Br:17]Br.C(OCC)(=O)C>C(O)(=O)C.O>[C:1]([O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([Br:17])[C:6]=1[O:15][CH3:16])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 6881894-formyl-2,6-dimethoxyphenyl acetate

Product 1

HCID 22633147HCID 22633147, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 4-acetoxy-3,5-dimethoxy benzaldehyde (5.4 g, 20 mmol) and 5.4 g (40 mmol) of NaOAc.3H2O in acetic acid (14 mL) and water (2 mL) was added dropwise bromine (1.2 mL, 24 mmol). The mixture was stirred at RT overnight and repartitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (3×) and the combined organic layer was washed with saturated sodium bicarbonate solution, water and brine and dried over anhydrous sodium sulfate. Removal of the solvent gave 5.6 g of 4-acetoxy-2-bromo-3,5-dimethoxybenzaldehyde (80%).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  2. washthe combined organic layer was washed with saturated sodium bicarbonate solution, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-40e2b32a56374d41af71a5110c0d8cbe
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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