ChemicalBook CAS DataBase List 18-Methoxy-18-oxooctadecanoic acid

18-Methoxy-18-oxooctadecanoic acid synthesis

8synthesis methods

Product Name:18-Methoxy-18-oxooctadecanoic acid
CAS Number:72849-35-5
Molecular formula:C19H36O4
Molecular Weight:328.49

1472-93-1

72849-35-5

The general procedure for the synthesis of monomethyl octadecanedioate from dimethyl octadecanedioate was as follows: compound 8 (5.8 mmol) was added to 0.07 M Ba(OH)? solution in anhydrous methanol (85 mL) and the reaction mixture was stirred at 40 °C for 24 hours. After completion of the reaction, the mixture was filtered under reduced pressure. The resulting precipitate was washed with ether and dissolved in deionized water. Subsequently, the solution was acidified to pH 3 with hydrochloric acid and extracted twice with dichloromethane. The organic phases were combined, the solvents were removed by vacuum evaporation and the resulting residue was purified by fast column chromatography using petroleum ether:ethyl acetate (8:2, v/v) as eluent to give the final compound 9 in 52% yield.

1472-93-1 Synthesis

1472-93-1
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$22.00/1g

72849-35-5
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$24.00/100mg

Yield: 86.8%

Reaction Conditions:

with methanol;barium(II) hydroxide at 20; for 48 h;

Steps:

1 Step 1: Synthesis of Intermediate 01-103-2
To a stirred solution of 01-103-1 (3 g, 8.76 mmol) in MeOH (15 mL) at RT was added slowly Ba(OH)2 (0.75 g, 4.4 mmol). The resulting mixture was stirred at RT. After 48 h, the reaction mixture was quenched with ice water, acidified with 1.5 M HCl, and extracted with EtOAc. The combined organic extract was washed with water, brine, dried over Na2SO4, and then evaporated to yield crude 01-103-2. Purification by column chromatography (10% EtOAc in petroleum ether) afforded 01-103-2 as an off-white solid (2.5 g, 86.8%).

References:

DTX PHARMA, INC. WO2021/108662, 2021, A1 Location in patent:Paragraph 0852