Question

Proposed Synthesis Show the structure of your target molecule as well as synthetic schemes illustrating the two steps required for preparing it from "allowed" starting materials. For each synthetic step indicate the source of the experimental procedure you will follow-sources can either be literature references or simply the course pack itself. (See the example below for the format to be followed) ~Example Target Molecule: NO2 Cl Step 1: OH Reference: Tetrahedron, 1990, 46, 2975 HNO3 Step 2 o H2SO4 NO2 Reference: Organic Lab Course Pack оснз Target Molecule Number: P4 Starting Materials: You will be allowed to obtain two "free" grams of starting materials. Additional grams of starting material can be "bought" at a "price" of two points on your write-up sheet. Names, structures, and hazard classes of available starting materials are indicated below: HaC pnyaetyde anline toxic) (toxic) toxic) toxic) но anthranilic acldp-anisic acid (nonhazardous) p-hydroxybenzaldehyde toxic) Reagents: The reagents listed below will be available, stored according to hazard class. Requests for reagents not listed below should be made at the time you submit your proposed synthetic may or may not be accommodated based on availability and cost. It is important to return all pipets and spatulas to the appropriate "holsters" on each reagent bottle in order to prevent reagents. and Hazard Class Hazard Class flammable solvent 1M sodium hydroxide corrosive (caustic) 3.0M sodium hydroxide corrosive (caustic) ether flammable solvent 10% sulfuric acid flammable solvent ethanol methanol flammable solvent acetic anhydride sodium bicarbonate nonhazardous acetic acid corrosive (organic) corrosive (oxidant) l corrosive (ondant) sodium chloride enesulfonic acid nonhazardous sodium thiosulfate nonhazardous odine sodium chloroacetate 10% bromine in acetic acid sodium borohydride water-reactive Before coming to lab: Plan which experiments you will be conducting each day and familiarize yourself with the procedures involved. You should have a definite plan of action for each day, based on the results of the previous lab period's experiments. If time and the nature of the reactions you are carrying out allow you to run two reactions in one day (in other words, immediately use the product of one reaction as the starting material for the next), you might want to consider doing this, for this will allow you additional time to either purify products or repeat any experiments that fail to give the desired product. Prepare your laboratory manual with the appropriate items- experiment details, purpose, chemical reaction, reagent table, and intended procedures. Note: One week prior to starting this experiment you must submit your planned synthetic approach to your lab instructor. All that is required is a reaction scheme showing the starting material you intend to use and the reagents necessary to ultimately convert it into the desired product (see the reaction scheme at the start of the bromoacetanilide synthesis experiment for an example). If desired, you can also supply your lab instructor with additional information regarding the reactions you intend to carry out (experimental procedures, etc.).

Answer 1

I understand that the target material is OCH3 он 2-(((4-methoxyphenyl)amino)methyl)phenol It can be easily synthesized from the 1-methoxy-4-nitrobenzene 1-methoxy-4-nitrobenzene OCH3 O2N Step l: Reduction of nitro group to amine Ref: Allen, C. F. H.; VanAllan, J. (1955). "2-Amino-p-cymene". Organic Syntheses.; Collective Volume, 3, p. 63 OCH3 OCH H2/ Raney Ni O2N H2N CH3OH 1-methoxy-4-nitrobenzene 4-methoxyaniline Step Il: The reductive amination of salicyladehyde with 4-methoxyaniline in presence of sodium borohydride by using B(OSO3H)3/Sio2(SBSA) as the reusable solid catalyst in acetonitrile or solvent free conditions OCH3 H2N NaBH4, r.t., CH3CN он 4-methoxyaniline 2-hydroxybenzaldehyde 2-(((4-methoxyphenyl)amino)methyl)phenol Ref: J. Chem. Sci. Vol. 129, No. 1, January 2017, pp. 75-80