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

Back to List

Log In

Join Now

Print Version


About this site

Privacy Policy

Copyright Syntheticpages ©2001

Ortho Fries rearrangement of 3-methylcatechol diacetate; 2, 3-dihydroxy-4-methylacetophenone

SyntheticPage 41 (2001)
Submitted 14th Aug 2001, published 15th Aug 2001

Jonathan Wilden ([email protected]),
A contribution from the Harrowven Group, Southampton

Reaction Scheme

Chemicals Used
3-Methylcatechol diacetate, Aluminium chloride (Lancaster).

Finely powdered 3-methylcatechol diacetate (25 g, 0.12 mol) and ground aluminium chloride (16.0 g, 0.12 mol) were mixed and heated to 90 oC for 5 minutes. The temperature was then raised to 120 oC and maintained at that temperature for 25 minutes. The resulting brown solid was allowed to cool and quenched by the addition of dilute HCl (200 mL) and extracted into dichloromethane (3 x 200 mL). The combined extracts were dried (MgSO4), filtered and the solvent removed from the filtrate in vacuo. The crude product was recrystallised from petrol to yield the acetophenone as a white solid (3.6 g, 22 mmol, 18%).

Author's Comments
After performing this reaction 3-4 times (always on a 25 g scale) we found that careful control of temperature is critical in this reaction. The reaction mixture must be at 90 oC for no more than 5 minutes and after this time should be heated rapidly (ie over 2-3 minutes) to 120 oC or else the para product may be observed.

MP: 65-67 C (petrol). Lit. 70 C (petrol) 1H NMR (300 MHz, CDCl3) 12.50 (1H, s), 7.19 (1H, d), 6.69 (1H, d), 5.80 (1H, s), 2.61 (3H, s), 2.31 (3H, s).

Lead Reference
Cullinane, N. M.; Edwards, B. F. R.; J. Chem. Soc., 1958, 2926.

Other References
Doppler, T.; Schmid, H.; Helv. Chim. Acta., 1979, 62, 314.

This page has been viewed approximately 553 times since records began.

Get CDX file

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 ©2005 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