The desymmetrisation of resorcinol: The synthesis of resorcinol monoalkyl ethers

Jonathan Y. Boxhall; Philip C. Bulman Page; Yohan Chan; Colin M. Hayman; Harry Heaney; Matthew J. McGrath

doi:10.1055/s-2003-39293

The desymmetrisation of resorcinol: The synthesis of resorcinol monoalkyl ethers

Jonathan Y. Boxhall
, Philip C. Bulman Page
, Yohan Chan
, Colin M. Hayman
, Harry Heaney
, Matthew J. McGrath

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

The desymmetrisation of resorcinol to give 3-alkoxyresorcinol derivatives can be achieved in excellent yields either from resorcinol monobenzoate and alcohols using Mitsunobu reactions followed by hydrolysis using a strong base or by using 3-iodophenylbenzyl ether as a resorcinol monobenzyl ether equivalent in reactions with alcohols catalysed by copper(I)-9,10-phenanthroline followed by ammonium formate-palladium catalysed hydrogenolysis.

Original language	English
Pages (from-to)	997-1001
Number of pages	5
Journal	Synlett
Issue number	7
DOIs	https://doi.org/10.1055/s-2003-39293
Publication status	Published - Jun 2003

Keywords

Mitsunobu reactions
ARYL
CALIX<4>RESORCINARENE DERIVATIVES
caesium carbonate
hydrolyses
ANALOGS
PHOSPHATE
KADSURENONE
9
copper(I) iodide
10-phenanthroline

Access to Document

10.1055/s-2003-39293

Cite this

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title = "The desymmetrisation of resorcinol: The synthesis of resorcinol monoalkyl ethers",

abstract = "The desymmetrisation of resorcinol to give 3-alkoxyresorcinol derivatives can be achieved in excellent yields either from resorcinol monobenzoate and alcohols using Mitsunobu reactions followed by hydrolysis using a strong base or by using 3-iodophenylbenzyl ether as a resorcinol monobenzyl ether equivalent in reactions with alcohols catalysed by copper(I)-9,10-phenanthroline followed by ammonium formate-palladium catalysed hydrogenolysis.",

keywords = "Mitsunobu reactions, ARYL, CALIX<4>RESORCINARENE DERIVATIVES, caesium carbonate, hydrolyses, ANALOGS, PHOSPHATE, KADSURENONE, 9, copper(I) iodide, 10-phenanthroline",

author = "Boxhall, \{Jonathan Y.\} and \{Bulman Page\}, \{Philip C.\} and Yohan Chan and Hayman, \{Colin M.\} and Harry Heaney and McGrath, \{Matthew J.\}",

year = "2003",

month = jun,

doi = "10.1055/s-2003-39293",

language = "English",

pages = "997--1001",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "7",

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T1 - The desymmetrisation of resorcinol: The synthesis of resorcinol monoalkyl ethers

AU - Boxhall, Jonathan Y.

AU - Bulman Page, Philip C.

AU - Chan, Yohan

AU - Hayman, Colin M.

AU - Heaney, Harry

AU - McGrath, Matthew J.

PY - 2003/6

Y1 - 2003/6

N2 - The desymmetrisation of resorcinol to give 3-alkoxyresorcinol derivatives can be achieved in excellent yields either from resorcinol monobenzoate and alcohols using Mitsunobu reactions followed by hydrolysis using a strong base or by using 3-iodophenylbenzyl ether as a resorcinol monobenzyl ether equivalent in reactions with alcohols catalysed by copper(I)-9,10-phenanthroline followed by ammonium formate-palladium catalysed hydrogenolysis.

AB - The desymmetrisation of resorcinol to give 3-alkoxyresorcinol derivatives can be achieved in excellent yields either from resorcinol monobenzoate and alcohols using Mitsunobu reactions followed by hydrolysis using a strong base or by using 3-iodophenylbenzyl ether as a resorcinol monobenzyl ether equivalent in reactions with alcohols catalysed by copper(I)-9,10-phenanthroline followed by ammonium formate-palladium catalysed hydrogenolysis.

KW - Mitsunobu reactions

KW - ARYL

KW - CALIX<4>RESORCINARENE DERIVATIVES

KW - caesium carbonate

KW - hydrolyses

KW - ANALOGS

KW - PHOSPHATE

KW - KADSURENONE

KW - 9

KW - copper(I) iodide

KW - 10-phenanthroline

U2 - 10.1055/s-2003-39293

DO - 10.1055/s-2003-39293

M3 - Article

SN - 0936-5214

SP - 997

EP - 1001

JO - Synlett

JF - Synlett

IS - 7

ER -