Submit a SyntheticPage About SyntheticPages Page Index Browse most recent SyntheticPages View the Leaderboard We value your feedback
SyntheticPages
  Navigation Buttons


Back to List

Log In

Join Now

Print Version

Home

About this site

Privacy Policy







Copyright Syntheticpages ©2001




t-Butyl acetate as a t-butyl cation equivalent: O-Alkylation of N-Hydroxyphthalimide; t-butoxyphthalimide

SyntheticPage 145 (2001)
Submitted 28th Aug 2001, published 28th Aug 2001

Andrew McCarroll ([email protected]),
A contribution from the Walton Group, St. Andrews



Chemicals Used
1,4-dioxane (300 ml), t-butyl acetate (75 ml; 0.56 mol), N-hydroxyphthalimide (8.15 g; 0.05 mol), 72% perchloric acid (0.5 ml).

Procedure
The reagents are mixed together (in order listed), and stirred in a stoppered flask for 24 hours at room temperature. Saturated aqueous sodium bicarbonate solution is added until there is no more effervescence (~200 ml). The organic layer is separated, and concentrated. The crystals are dissolved in ether, dried and concentrated, then recrystallised (40/60 Petrol). Yield: 8.81 g; 80%.

Author's Comments
The reference that the procedure was taken from (see below) was in Russian, and our translation indicated that the dioxane layer should be extracted with DCM, but the solvents were miscible, so the method described was used. A first attempt, in which the mixture turned blood-red, failed for unknown reasons and the successful attempt seemingly followed the same procedure. The technique was used because the usual way to prepare N-alkoxyphthalimides, Mitsonobu condensation ([SyntheticPage 122] ), failed.

Data
m.p. 110.5-113 oC. (lit 110-111 oC; Chimiak and Kolasa)1H nmr (300 MHz, CDCl3) 1.43 (9H,s), 7.65-7.85 (4H, ArH)


Lead Reference
A. J. McCarroll and J. C. Walton, J. Chem. Soc. Perkin Trans. 2, 2000, 1868.

Other References
A. Chimiak, T. Kolasa. Rocz. Chem., 1974, 48, 139. t-Butyl acetate is reported to be a good general t-butylating agent in the presence of a strong acid. E. Taschner, Cz. Wasielewski, J. F. Biernat, Ann., 1961, 646, 119.

This page has been viewed approximately 120 times since records began.

Get CDX file (Choose "Open this file from its current location" TWICE)

SyntheticPagesTM are for use exclusively by those with training and experience in synthetic chemistry. While contributors are asked to identify hazards and to use methods designed to reduce risk, no formal hazard or risk assessments are included, and these procedures must be conducted at one's own risk. SyntheticPages, its editors, owners and associates do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. Copyright ©2004 Synthetic Pages

Comment on this page!

Registered users may add comments to other pages. If you have already registered, please log in, otherwise you may register here.

Back to List

Back to Top

By using this site, you agree to its Terms and Conditions