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ChemicalBook CAS DataBase List METHYL 4-FLUORO-3-HYDROXYBENZOATE
214822-96-5

METHYL 4-FLUORO-3-HYDROXYBENZOATE synthesis

7synthesis methods
51446-31-2 Synthesis
4-FLUORO-3-HYDROXYBENZOIC ACID

51446-31-2
213 suppliers
$6.00/250mg

-

Yield: 99%

Reaction Conditions:

with sulfuric acid;sodium hydrogencarbonate;trimethyl orthoformate in methanol

Steps:

1 Preparation of Methyl 4-fluoro-3-hydroxybenzoate (Compound (III))
EXAMPLE 1 Preparation of Methyl 4-fluoro-3-hydroxybenzoate (Compound (III)) 4-Fluoro-3-hydroxybenzoic acid (20.0 g, 0.13 mol) was dissolved in anhydrous methanol (160 mL), mixed with trimethyl orthoformate (25 mL) followed by the addition of concentrated H2SO4 (3 mL) and the reaction was heated to 40-55° C. overnight. Half of the solvent was removed in vacuo, the remaining solution was poured into an ice/H2O mixture and the product was extracted twice with diethyl ether. The combined ether phases were washed twice with H2O, treated with a cold solution of saturated NaHCO3, treated with brine, dried with MgSO4, filtered, and the solvent was removed in vacuo to give 21.6 g (99% yield) of a white solid as the title compound (mp 93.5-94.5° C.). Mass spectrum (70 eV) m/z (relative intensity) 170 (44, M+), 139 (100), 111 (83), 83 (83), 82 (16), 81 (11), 63 (11), 57 (24).

References:

Astra Aktiebolag US6197978, 2001, B1

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