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ChemicalBook CAS DataBase List methyl 4-(hydroxymethyl)-3-methylbenzoate
24078-25-9

methyl 4-(hydroxymethyl)-3-methylbenzoate synthesis

2synthesis methods
24078-24-8 Synthesis
Methyl 4-formyl-3-methylbenzoate

24078-24-8
45 suppliers
$515.00/1g

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Yield:24078-25-9 84%

Reaction Conditions:

with sodium tetrahydroborate in methanol at 0 - 20; for 0.5 h;

Steps:

18.C Methyl 4-(hydroxymethyl)-3-methylbenzoate (18-4B).

To a stirred solution of 18-3B (1.4 g, 7.8 mmol) in MeOH, was added NaBH4 (0.29 g, 7.8 mmol) at 0 °C and stirred to RT for 30 min. After consumption of starting material (TLC), reaction mixture was quenched with saturated ammonium chloride solution, then MeOH was distilled off and aqueous layer was extracted with EtOAc, dried over Na2S04 and concentrated at reduced pressure. The crude product was purified by flash column chromatography (100-200 silica) using 20% EtOAc in hexane to afford 18-4B (1.2 g, 6.6 mmol, 84% yield) as a colorless liquid. MS (ESI): m/z 181.0 (M+l)+.

References:

WO2016/154241,2016,A1 Location in patent:Paragraph 560; 564