A facile demethylation of ortho substituted aryl methyl ethers promoted by AlCl3

被引:24
作者
Du, Zhen-Ting [1 ]
Lu, Jing [1 ]
Yu, Hong-Rui [1 ]
Xu, Yan [1 ]
Li, An-Pai [2 ]
机构
[1] NW A&F Univ, Coll Sci, Yangling 712100, Shaanxi, Peoples R China
[2] Synthet Technol Pte Ltd, Singapore 048693, Singapore
基金
中国国家自然科学基金;
关键词
demethylation; aluminium chloride; phenol methyl ethers; nimbosidione; ALKYL ETHERS; ACID; CLEAVAGE; DEPROTECTION; SYSTEM;
D O I
10.3184/030823410X12708998015900
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
An efficient and practical demethylation of ortho substituted aryl methyl ethers using AlCl3 has been developed. This method gives a high conversion, is simple to operate and is cost-effective. A mechanism involving the complexation of AlCl3 with the OMe and the adjacent electron withdrawing group is proposed. Many functional groups can be tolerated in the demethylation process, and 29 examples gave a demethylated product in a yield of 90-98%.
引用
收藏
页码:222 / 227
页数:6
相关论文
共 21 条
[1]
SYNTHESIS OF NITROPHENOLS [J].
ANDERSON, JS ;
BROWN, KC .
SYNTHETIC COMMUNICATIONS, 1983, 13 (03) :233-236
[2]
3 NEW DITERPENOIDS FROM THE STEM BARK OF AZADIRACHTA-INDICA [J].
ARA, I ;
SIDDIQUI, BS ;
FAIZI, S ;
SIDDIQUI, S .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (04) :816-820
[3]
CLEAVAGE OF ETHERS [J].
BHATT, MV ;
KULKARNI, SU .
SYNTHESIS-STUTTGART, 1983, (04) :249-282
[4]
Diphenyl disulfide and sodium in NMP as an efficient protocol for in situ generation of thiophenolate anion: Selective deprotection of aryl alkyl ethers and alkyl/aryl esters under nonhydrolytic conditions [J].
Chakraborti, AK ;
Nayak, MK ;
Sharma, L .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1776-1780
[5]
Photohydrodimerization of 6-methoxyflavone to 6,6"-dimethoxy-2,2"-biflavanones [J].
Chen, AH ;
Kuo, WB ;
Chen, CW .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2004, 51 (06) :1389-1394
[6]
Du ZT, 2004, J CHEM RES, P427
[7]
Facile total synthesis of (±)-nimbol [J].
Du, ZT ;
Yue, GR ;
Li, AP ;
Ma, JY ;
Wu, TX ;
She, XG ;
Pan, XF .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2004, 51 (03) :505-508
[8]
Spectroscopic investigations of new binuclear transition metal complexes of Schiff bases derived from 4,6-diacetylresorcinol and 3-amino-1-propanol or 1,3-diamino-propane [J].
Emara, Adel A. A. ;
Saleh, Akila A. ;
Adly, Omima M. I. .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2007, 68 (03) :592-604
[9]
Feutrill G. I., 1970, TETRAHEDRON LETT, V11, P1327
[10]
REGIOSELECTIVE CLEAVAGE OF AROMATIC METHYL ETHERS BY METHANESULPHONIC ACID IN PRESENCE OF METHIONINE [J].
FUJII, N ;
IRIE, H ;
YAJIMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (20) :2288-2289