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29th April 2015 @ 01:10

With Paul King an excellent undergraduate student working with Alice on Wednesday's in the lab at USyd.

GitHub Issue #235 and #236


Procedure:

DL-Mandelic acid (10.0 g, 35.4 mmol, 1 equiv.) and pTsOH (114 mg, 0.66 mmol, 0.01 equiv.) were dissolved in MeOH (132 mL) and the reaction mixture was heated to reflux for 3 h.

Solvent was removed in vacuo to yield a colourless oil (11 g, quantitative) NO NMR taken - looked at Paul's TLC and no SM so submitted directly to THP protection.

Data:

 

Hazard and Risk Assessment:

HIRAC AEW 173-1.pdf

InChi:

InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)

to 

InChI=1S/C9H10O3/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8,10H,1H3


Literature:

Following this procedure:

Favre A, Carreauz F, Deligny M, Carboni B (2008) Stereoselective Synthesis of (+)-Goniodiol, (+)-Goniotriol, (–)-Goniofupyrone, and (+)-Altholactone Using a Catalytic Asymmetric Hetero-Diels–Alder/Allylboration Approach. Eur. J. Org. Chem. 29: 4900–4907. doi: 10.1002/ejoc.200800535