METHYL 3-HYDROXY-4-(HYDROXYMETHYL)BENZOATE synthesis
- Product Name:METHYL 3-HYDROXY-4-(HYDROXYMETHYL)BENZOATE
- CAS Number:71780-40-0
- Molecular formula:C9H10O4
- Molecular Weight:182.17
6342-72-9
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Yield:71780-40-0 85%
Reaction Conditions:
with sodium tetrahydroborate in tetrahydrofuran; for 2 h;Reflux;
Steps:
2.1 Step 1. Methyl 3-hydroxy-4-(hydroxymethyl)benzoate
To a solution of 500 mg (2.38 mmol) dimethyl hydroxyterephthalate in 5 mL THF was added 180 mg (4.76 mmol, 2 eq) sodium borohydride and the resulting suspensionwas heated at reflux for 2 h. The solvent was removed in vacuo and 5 mL of water wasadded to the resulting residue. The solution was then acidified with 1M HCl and stored at0 oc until crystallization was observed. The product was purified by columnchromatography and 368 mg (2.02 mmol, 85%) of the product was obtained as a white solid. Rf(25% EtOAc, 75% Hexanes) = 0.11; 1H NMR (600 MHz, DMSO-d6) 8 9.83 (s,1H), 7.42 (dt, J = 3.3, 1.9 Hz, 2H), 7.36 (q, J = 1.6 Hz, 1H), 5.16 (s, 1H), 4.51 (s, 2H),3.81 (dd, J = 2.2, 1.1 Hz, 3H). 13C NMR (126 MHz, DMSO-d6) 8 167.24, 154.83, 135.52,129.49, 127.85, 120.75, 115.56, 58.90, 52.87. HRMS: m/z (+Na+). calc'd: 205.0471,found: 205.0471.
References:
WO2018/191360,2018,A1 Location in patent:Page/Page column 62; 63
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