ChemicalBook CAS DataBase List 4-Methoxyphthalic acid

4-Methoxyphthalic acid synthesis

13synthesis methods

Product Name:4-Methoxyphthalic acid
CAS Number:1885-13-8
Molecular formula:C9H8O5
Molecular Weight:196.16

22895-19-8 Synthesis

DIMETHYL 4-METHOXYBENZENE-1,2-DICARBOXYLATE

22895-19-8
19 suppliers
$297.00/10ml-f

1885-13-8
103 suppliers
$8.00/100mg

Yield: 99%

Reaction Conditions:

Stage #1:dimethyl 4-methoxyphtalate with potassium hydroxide;water in methanol for 4 h;Heating / reflux;
Stage #2: with hydrogenchloride in water; pH=<= 2

Steps:

C.C2
A solution of dimethyl 4-methoxyphthalate (36.75 g, 0.16 mol) in methanol (100 ml) was treated with a solution of potassium hydroxide (28.0 g, 0.5 mol) in water (50 ml) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol was removed in vacuo and the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid. The solid material was filtered off, washed with water and sucked dry under reduced pressure overnight to afford 4-methoxyphthalic acid (31.8 g, 99%) as an off white solid. ¹H NMR (DMSOd₆) 12.90 (2H, br s), 7.74 (1H, d), 7.12-7.05 (2H₁ m), 3.84 (3H, s). MS: [M+H]⁺ 197.

References:

ASTEX THERAPEUTICS LIMITED WO2008/44029, 2008, A1 Location in patent:Page/Page column 203

201230-82-2 Synthesis