Hydrochloric Acid → 3-Hydroxy-1-naphthoic acid

반응식

C[O:2][C:3]1[CH:4]=[C:5]([C:13]([O:15]C)=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.Cl.[NH+]1C=CC=CC=1.Cl>>[OH:2][C:3]1[CH:4]=[C:5]([C:13]([OH:15])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 21584435Pyridinium hydrochloride

HCID 22452641Methyl 3-methoxy-1-naphthoate

생성물 1

HCID 1902323-Hydroxy-1-naphthoic acid수율 94.3%

실험 절차

Methyl 3-methoxy-1-naphthalenecarboxylate (Bin Ye and Terrence R. Burke, Tetrahedron, 52, 9963-9970 (1996)) (8.13 g, 37.6 mmol) and pyridinium hydrochloride (217 g, 1.88 mol) was heated to 200° C. for 30 min. After cooling to room temperature, 1N HCl was added and the precipitate was filtered and washed with water to give the title compound (6.67 g, 94%) as a yellow solid. 1H-NMR (DMSO-d6): 13.16 (s, 1H), 10.03 (s, 1H), 8.73 (d, 1H), 7.78 (d, 1H), 7.72 (d, 1H), 7.37 (m, 3H); MS m/z 187 (M−H).