ChemicalBook CAS DataBase List 1-BENZOFURAN-6-OL

1-BENZOFURAN-6-OL synthesis

14synthesis methods

Product Name:1-BENZOFURAN-6-OL
CAS Number:13196-11-7
Molecular formula:C8H6O2
Molecular Weight:134.13

50551-63-8 Synthesis

50551-63-8
56 suppliers
$62.00/100mg

13196-11-7
99 suppliers
$185.00/250mg

Yield: 90%

Reaction Conditions:

with sodium dodecanethiolate in N,N-dimethyl-formamide at 130; for 3 h;Large scale;Temperature;Reagent/catalyst;

Steps:

6-Hydroxybenzofuran (1)
DMF (18 L), sodium dodecanethiolate (7.6 kg, 33.9 mol), and 4 (2.95 kg, 19.9 mol)were added to a 50-L reactor. The reaction mixture was heated and stirred at 130 Cfor 3 h, then cooled to rt, and 4 N NaOH was added to adjust the pH to 13. Thesolution was extracted with petroleum ether three times. The aqueous phase was acidified with 2 N HCl to pH 2 and extracted with ethyl acetate three times. Theethyl acetate phases were combined, washed with water, and dried over sodiumsulfate. The solvent was removed under vacuum and the residue was left overnightat room temperature to afford 1 as a light brown solid (2.65 kg, 90 % yield, 99.5 %purity), m.p. 54-56 C. 1H-NMR (CDCl3, ppm): d 7.55 (s, 1H), 7.44-7.46 (d, 1H),7.03 (s, 1H), 6.81-6.83 (d, 1H), 6.72 (s, 1H), 5.09 (br, 1H).

References:

Song, Shu-Yong;Lu, He-Lin;Wang, Gui-Fei;Yang, Yi-Qiu;Huang, Yun-Sheng [Research on Chemical Intermediates,2016,vol. 42,# 5,p. 4433 - 4442]