Benzoic acid, 5-(hydroxymethyl)-2-methyl-, methyl ester synthesis

7synthesis methods

Product Name:Benzoic acid, 5-(hydroxymethyl)-2-methyl-, methyl ester
CAS Number:72985-24-1
Molecular formula:C10H12O3
Molecular Weight:180.2

675148-96-6 Synthesis

675148-96-6
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Benzoic acid, 5-(hydroxymethyl)-2-methyl-, methyl ester

72985-24-1
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Yield:72985-24-1 95%

Reaction Conditions:

with diborane in tetrahydrofuran at 20; for 4 h;

Steps:

jlntermediate 54J - Methyl 5-(hydroxymethyl)-2-methylbenzoate

Methyl 5-formyl-2-methylbenzoate jlntermediate 35J (367 mg, 2.06 mmol) was dissolved in anhydrous tetrahydrofuran (5 ml) then borane (1M in THF, 4.32 ml) was added and the reaction was stirred at ambient temperature for 4 hours. The reaction was partitioned between 1:1 sat aq NH4C1 / water (10 ml) and DCM (10 ml) then the organics were separated, dried over Na2SO4, filtered and concentrated in vacuo to yield the title compound as a light yellow oil (387 mg, 95%).1H NIVIR (500 IVIFIz, DMSO-d6) 7.78 (d, J = 1.5 Hz, 1H), 7.40 (dd, J = 7.8, 1.7 Hz, 1H), 7.27 (d, J = 7.8 Hz, 1H), 5.26 (t, J = 5.7 Hz, 1H), 4.49 (d, J = 5.7 Hz, 2H), 3.82 (s, 3H), 2.48 (s, 3H). LCMS Method 2 - Tr = 0.90 mm (ES+) (M+H) 163.35

References:

WO2018/89433,2018,A1 Location in patent:Paragraph 00335

75-75-2 Synthesis