ChemicalBook CAS DataBase List METHYL 4-FLUORO-3-HYDROXYBENZOATE

METHYL 4-FLUORO-3-HYDROXYBENZOATE synthesis

7synthesis methods

Product Name:METHYL 4-FLUORO-3-HYDROXYBENZOATE
CAS Number:214822-96-5
Molecular formula:C8H7FO3
Molecular Weight:170.14

51446-31-2 Synthesis

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

214822-96-5
94 suppliers
$18.00/1g

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

67-56-1 Synthesis