Regioselective demethylation of 2,6-dimethoxybenzaldehydes with magnesium iodide etherate

Tetrahedron Letters

Volumn 40, Issue 41, 1999, Pages 7363-7365

  Yamaguchi, Seiji ^a   Nedachi, Masahiro ^a   Yokoyama, Hajime ^a   Hirai, Yoshiro ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Deblocking; Magnesium; Magnesium compounds; Phenols; Regiocontrol

Indexed keywords

BENZALDEHYDE DERIVATIVE; MAGNESIUM; MAGNESIUM DERIVATIVE; METHYL GROUP; SALICYLALDEHYDE;

ARTICLE; DEALKYLATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033536670     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01411-2     Document Type: Article

References (7)

1. 1. Yamaguchi, S.; Sugiura, K.; Fukuoka, R.; Okazaki, K.; Takeuchi, M.; Kawase, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3607.
2. 2. Yamaguchi, S.; Takai, M.; Hanazome, I.; Okada, Y; Kawase, Y. Bull. Chem. Soc. Jpn. 1987, 60, 3603.
3. 3. Compounds 2g and 3g were prepared by chlorination of corresponding salicylaldehydes with sulfuryl chloride, and these details will be reported soon in our synthetic study on mycochromenic acid.
4. 4. Details will be reported soon in our synthetic study on mycochromenic acid.
5. 5. General procedure for demethylation: To a benzene solution of magnesium iodide etherate, prepared from magnesium metal (102 mg, 3.99 mmol), iodine (936 mg, 3.62 mmol), ether (6 ml), and benzene (10 ml), was added a solution of 2,6-dimethoxybenzaldehyde (3 mmol) in benzene (30 ml); the mixture was refluxed, treated with 10% hydrochloric acid, and extracted with benzene, and the product was purified on a silica gel column.
6. 6. Details will be reported soon in our synthetic study on cannabiorcichromenic acid.
7. 7. Yamaguchi, S.; Shouji, N.; Kuroda, K. Bull. Chem. Soc. Jpn. 1995, 68, 305.