ChemicalBook CAS DataBase List 2,4-dihydroxy-6-propyl-benzoic acid methyl ester

2,4-dihydroxy-6-propyl-benzoic acid methyl ester synthesis

8synthesis methods

Product Name:2,4-dihydroxy-6-propyl-benzoic acid methyl ester
CAS Number:55382-52-0
Molecular formula:C11H14O4
Molecular Weight:210.23

2,4-Dihydroxy-6-propylbenzoic acid was dissolved in methanol, and then a catalytic amount (a few drops) of concentrated sulfuric acid was added. The esterification reaction took place, followed by removal of the solvent. The resulting crude product was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and then with saline. The organic layer was then dried using magnesium sulfate. The product was concentrated and subjected to purification using silica gel column chromatography. Finally, product A was obtained after the purification process. 2,4-dihydroxy-6-propyl-benzoic acid methyl ester

2,4-dihydroxy-6-propyl-benzoic acid methyl ester

5609-09-6 Synthesis

5609-09-6
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108-59-8 Synthesis

108-59-8
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55382-52-0
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Yield:-

Reaction Conditions:

Stage #1: trans 3-hepten-2-one;malonic acid dimethyl esterwith sodium in methanol at 0; for 8 h;Reflux;
Stage #2: with bromine in N,N-dimethyl-formamide at 0 - 80; for 17 h;

Steps:

1B Example 1B

A solution of methanol (450 mL) at 0 °C was treated with sodium (25.5 g, 1 .1 1 mol) in portions and stirred until dissolved. Dimethyl malonate (143 mL, 1 .25 mol) was then added followed by (￡)-hept-3-en-2-one (100 g, 0.89 mol) and the solution heated at reflux for 8 h. The methanol was removed then diluted with water (600 mL) and washed with CHCI₃ (500 mL). The aqueous later was acidified and extracted with CHCI₃ (3 x 400 mL). The combined organic layers were dried (MgS0₄) and concentrated to give a white solid. The white solid (5.37 g, 25.3 mmol) was dissolved in DMF (12 ml) and cooled to 0 °C. A solution of Br₂ (1 .30 mL, 25.4 mmol) in DMF (6.6 mL) was slowly added and the solution stirred at 20 °C for 1 h. The solution was then heated to 80 °C for 16 h before cooling and treatment with 5% Na₂S₂0₃ aqueous solution (200 mL) and being extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried (MgS0₄) and concentrated. The crude material was recrystallized from DCM/hexane to give a white solid

References:

WO2019/33168,2019,A1 Location in patent:Page/Page column 17

67-56-1 Synthesis