ChemicalBook CAS DataBase List 2,5-DIMETHYL-3-FUROIC ACID

2,5-DIMETHYL-3-FUROIC ACID synthesis

8synthesis methods

Product Name:2,5-DIMETHYL-3-FUROIC ACID
CAS Number:636-44-2
Molecular formula:C7H8O3
Molecular Weight:140.14

29113-63-1 Synthesis

29113-63-1
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$156.00/50mg

636-44-2
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$13.00/500mg

Yield:636-44-2 92%

Reaction Conditions:

with sodium hydroxide in methanol at 60; for 2 h;

Steps:

7.3 5-(tertButyl)-2-methylfuran-3-carboxylic acid (3a) and 2,5-dimethylfuran-3-carboxylic acid (3b)
A stirred solution of ethyl 5-tertbutyl-2-methylfuran-3-carboxylate 2a (2.16g, 10.27mmol) or ethyl 2,5-dimethylfuran-3-carboxylate 2b (1.73g, 10.27mmol) in anhydrous methanol (30mL) was added with 2M sodium hydroxide solution (10.27mL, 20.55mmol) at 60°C for 2h, after the anhydrous methanol was removed under reduced pressure, adjusted to pH 1. A lot of precipitated white solid was filtered and dried in vacuo at 40°C for 24h to give a light white solid. 3a (1.57g, yield: 83.9%), mp: 88.2-91.5°C; MS (ESI) m/z (%): 180.8 [M-H]^-; 3b (1.32g, yield: 92.0%); mp: 136.0-138.4°C; MS (ESI) m/z (%): 138.8 [M-H]^-. ¹H NMR (DMSO-d₆, 300 MH): δ 2.18 (s, 3H), 2.43 (s, 3H), 6.18 (s, 1H), 12.34 (s, 1H).

References:

Zhao, Dongmei;Sun, Bin;Ren, Jinhong;Li, Fengrong;Song, Shuai;Lv, Xuejiao;Hao, Chenzhou;Cheng, Maosheng [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 6,p. 1356 - 1365]

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