To get access to the corresponding 2-acetyloky)-3-chloro- benzoic acid 21, we tr

Question

To get access to the corresponding 2-acetyloky)-3-chloro- benzoic acid 21, we treated 3-chloro-2-hydroxy benzoic acid 20 with acetic anhydride (Acro) in the presence of a catalytic amount of sulfuric acid, as shown in Scheme 1. CH3 Scheme 1. Synthesis of 21 Reagents and conditions a) CH,coho, H,so. neat, 140 C 2 h, 43%. Preparation of 2-(Acetyloxy)3-chlorobenzoic acid (21 concentrated H2SO (5 ml) was added to a stirred solution acid (20) (5.18 g,x mol) in acetic for anhydride (75 ml). The reaction mixture was heated to 140 Cand stirred at this temperature 2 h. The reaction mixture was allowed to cool to room temperature and poured into Hzo. After saturating with NaCI, the aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with water and brine, dried over Mgso, filtered, and concentrated in vacuo. Column chromato GsohexanelEtoAd formic acid, 5:1:0.1) afforded (21) XX g 43%) as a white solid. 2) (5 points) How many moles of 3-chloro-2-hydroxybenzoic acid were used? 3) (5 points) What is the molecular weight of the product 2-acetyloxy-3-chlorobenzoic acid?

Explanation / Answer

= 5.18 g/ 172.57 g mol-1 = 0.03 mol

n = 0.03 mol x 214.6 g mol-1 = 6.44 g

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