EXP+015



=Objective= To convert [|adrenaline] to a [|catechol aldehyde] using acid catalysis. How this fits into the synthesis of anti-malarials is described [|here].

=Procedure= Taken from [|Preparation and Properties of p-Hydroxyphenylacetaldehyde and 3-Methoxy-4-Hydroxyphenylacetaldehyde by Jay H. Robbins Archives of Biochemistry and Biophysics.] A solution of [|adrenaline] (217 mg, 1.18 mmol) in 85% phosphoric acid (6 mL) was heated in a 12mL **//Was it 10mL or 12mL? Compare to log.//** vial to 120C in a glycerol bath then removed from heat and allowed to cool for 30 seconds then added to water (36 mL) and then saturated with NaCl, followed by extraction with ether (17mL, 10mL, 10mL). **//Add in the TLC preformed at 19:30 on 06/22, as well as the NMR that was taken.//**

=Results= [|Video of set up]

Characterization
Two stains were done without a TLC run [|Ninhydrin stain] [|Anisaldehyde stain] [|Run in pure methanol] visible with iodine.

[|HNMR] was obtained of the product after it was re-dissolved with ether, dried with MgSO4, and vacuumed again to have a net weight of 15mg. There is no carbonyl peak that I can see and the NMR seems skewed. There is an [|expanded version] as well.

=Discussion= Based on the lack of an aldehyde proton in the 9-10 ppm range, it does not look like any aldehyde was isolated.

=Conclusion= Based on the NMR, the aldehyde was not produced however the reaction will be attempted once more.

=Log=

2006-06-22
16:55] turn on hot plate to heat glycerol 17:10] put phosphoric solution in 10mL vial and then in heated glycerol bath 17:23] solution heated to 120C, taken off of heat and cooled for 30seconds. added to 36mL distilled water. 19:00] Saturated with NaCl(didn't filter) 19:13] Poured solution without excess NaCl into a separatory funnel. Extracted with 17mL anhydrous ether 19:20] Extracted with 10mL anhydrous ether 19:24] Extracted with 10mL ether 19:30] Performed TLC 1:1 methylene chloride hexanes (no movement), pure methylene chloride (no movement), pure methanol (some movement) Ninhydrin and Ansaldehyde stains give little information.

2006-06-23
rotovaped ether extracts

2006-06-26
vacuumed off remains from rotovap. wt=15mg dry product would not dissolve in methylene chloride but did disolve in methanol TLC of 1:1 methylene chloride in hexanes showed nothing. Methanol had same movement =Tags= [|Adrenaline]InChI=1/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3 [|DOPAL] InChI=1/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2

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