Abstract
The isomeric 3-(hydroxyphenyl)propane-1, 2-diols have been synthesised from allylic precursors by epoxidation and cleavage. Several different methods have been examined for obtaining 1-(methoxyphenyl)propane-1, 3-diols. 2-(methoxyphenyl)propane-1, 3-diols and certain hydroxy analogues have been obtained from benzaldoximes converted by oxidation to methoxy- and benzyloxynitromethylbenzenes followed by hydroxymethylation with formaldehyde and catalytic hydrogenation.
Keywords
References
1.
Part 41a:
Payne P.
,
Tyman J.H.P.
,
Mehet S.K.
, and
Ninagawa A.
, J. Chem. Res. , 2006 , 402 .
2.
Boesekin J.
, Ber. , 1913 , 46 , 2612 –2628 .
3.
Mellon M.G.
, and
Morris V.N.
, Ind. Eng. Chem. , 1924 , 16 , 123 .
4.
Vinogradov E.E.
, Zh. Strukt. Khim , 1962 , 7 , 2813 .
5.
Tyman J.H.P.
, and
Mehet S.K.
, Chem. Phys.of Lipids , 2003 , 126 , 177 .
6.
Brown C.G.
, and
Sanderson B.R.
, Chem. Ind. , 1978 , 68 .
7.
Havinghorst C.R.
, Chem Eng. , 1963 , 70 , 228 .
8.
Jones M.M.
, and
Nyssen G.A.
, J. Inorg. Nucl. Chem. , 1978 , 40 , 1235 .
9.
Ebraheem K.A.K.
,
Al-Duhan J.A.
, and
Hamdi S.T.
, Eur. Polym. J. , 1985 , 21 , 97 .
10.
Ward W.J.
, US Patent, 6114484, (5 Sept. 2000 ).
11.
Uchida M.
,
Nishida K.
,
Kosako S.
, and
Urata T.
, Jpn. Kokai Koho JP2004, 227844.
12.
Burgoyne W.F.
, US Patent Appln., 14921, (20 Jan, 2005 ).
13.
Payne P.B.
, Ph D Thesis , Brunel University , 1992 .
14.
Brown H.C.
,
Kim S.C.
, and
Krisnamurthy S.J.
, J Org. Chem. , 1980 , 45 , 1 .
15.
Niederl J.B.
,
Roth R.T.
, and
Plentl A.A.
, J. Am. Chem. Soc. , 1937 , 59 , 1901 .
16.
Vogel A.I.
, A Textbook of Practical Organic Chemistry , 3rd. Edn., Longmans , 1956 .
17.
Kenner G.W.
, and
Williams N.R.
, J. Chem. Soc. , 1955 , 522 .
18.
Baylis C.J.
,
Odle S.W.D.
, and
Tymsn J.H.P.
, J. Chem. Soc., Perkin 1 , 1981 , 132
19.
Sharpless K.B.
, and
Young M.W.
, J. Org. Chem. , 1975 , 40 947 .
20.
Hurd C.D.
, and
Jenkins W.W.
, J. Org. Chem. , 1957 , 22 , 1418 .
21.
Strube R.E.
, Org. Syn. Coll Vol IV , 1963 , 417 .
22.
Wieranga W.
, and
Skulnick H.I.
, J Org. Chem. , 1979 , 44 , 310
23.
Ireland R.E.
, and
Marshall J.A.
, J. Am. Chem. Soc. , 1960 , 81 , 2907 .
24.
Brown H.C.
, and
Sim S.C.
, J Org. Chem. , 1984 , 49 , 1064
25.
Durrani A.A.
,
Goh C.S.
, and
Tyman J.H.P.
, Lipids , 1982 , 17 , 561 .
26.
Caplin J.
, and
Tymam J.H.P.
, J. Chem. Res. , 1982 , (S), 34 ; (M), 0321.
27.
Barnes A.
, and
Bush M.W.
, J. Am. Chem. Soc. , 1959 , 81 , 4705 .
28.
Emmons W.D.
, and
Pagano A.S.
, J. Am. Chem. Soc. , 1955 , 77 , 4557 .
29.
Steifel F.J.
, US Patent, 4868327 (19 Sept. 1989 ).