ChemicalBook CAS DataBase List methyl 2,4-dihydroxy-6-pentylbenzoate

methyl 2,4-dihydroxy-6-pentylbenzoate synthesis

9synthesis methods

Product Name:methyl 2,4-dihydroxy-6-pentylbenzoate
CAS Number:58016-28-7
Molecular formula:C13H18O4
Molecular Weight:238.28

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108-59-8 Synthesis

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Yield:-

Reaction Conditions:

Stage #1: (E)-non-3-en-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:

1A Example 1A

A solution of methanol (250 mL) at 0 °C was treated with sodium (12.0 g, 0.52 mol) in portions and stirred until dissolved. Dimethyl malonate (67.7 mL, 0.59 mol) was then added followed by (E)-non-3-en-2-one (59 g, 0.42 mol) and the solution heated at reflux for 8 h. The methanol was removed then diluted with water (400 mL) and washed with CHCI₃ (300 mL). The aqueous later was acidified and extracted with CHCI₃ (3 x 250 mL). The combined organic layers were dried (MgS04) and concentrated to give a white solid. The white solid (8.17 g, 34.0 mmol) was dissolved in DMF (20 ml) and cooled to 0 °C. A solution of Br₂ (1 .75 mL, 34.0 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 1 6 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 16