1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone synthesis

12synthesis methods

Product Name:1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone
CAS Number:94190-89-3
Molecular formula:C11H14O5
Molecular Weight:226.23

Preparation by Fries rearrangement of 1,2-dihydroxy-3,5-dimethoxybenzene dipropionate with aluminium chloride in methylene chloride at r.t. for 3 h (94%).

1-(2,3,4,6-Tetramethoxyphenyl)-1-propanone

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1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone

94190-89-3
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$1320.00/250mg

Yield:94190-89-3 85%

Reaction Conditions:

with boron trichloride in dichloromethane at 0 - 20; for 20 h;regioselective reaction;

Steps:

1-(2-Hydroxy-4,6-dimethoxy-3-methoxymethoxyphenyl) propan-1-one (5)

To a stirred suspension of compound 10 (0.850 g, 3.34 mmol) was dissolved in dry CH₂Cl₂ (5 mL) at 0 ^oC. A 1N BCl₃solution in CH₂Cl₂(13.0 mL) was added and the reaction mixture was allowed to warm up to room temperature and was left at room temperature for 20 h. Subsequently, the reaction mixture was poured into 30 ml of water and 20 ml of CH₂Cl₂ were added. The resulting mixture was filtered over celite, the organic Phase was collected and the aqueous phase was extracted twice with 20 ml of CH₂Cl₂. The combined organic layers were washed with 30 mL of water and dried over anhydrous Na₂SO₄and concentrated in vacuo, the residue was purified by column chromatography using (30% EtOAc/hexane) to afford the pure ketodiol (0.641 g, 85%) as a yellow solid.