Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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1.The actual yield of Compound (4) is 1.0g. What is the Theoretical Yield and the
Percent Yield of Compound (4)?
rOCH CH3
OCH,CH3
Esterase
OR
OH
ethyl 3-hydroxybenzoate (2)
ethyl 3-acetoxybenzoate (3)
3-acetoxybenzoic acid (4)
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Transcribed Image Text:1.The actual yield of Compound (4) is 1.0g. What is the Theoretical Yield and the Percent Yield of Compound (4)? rOCH CH3 OCH,CH3 Esterase OR OH ethyl 3-hydroxybenzoate (2) ethyl 3-acetoxybenzoate (3) 3-acetoxybenzoic acid (4)
ÓH
(1)
Ac20 / H3PO4 / 75°C
ČH3
(4)
Scheme 2:
Acylation of (1)
To a stirred solution of hydroxybenzoic acid 1 (1.0 g, 7.2 mmol) and acetic anhydride (2.5 mL,
26.4 mmol, 3.7 equivalents) was added 3 drops of concentrated phosphoric acid. The
solution was stirred and warmed to 75°C on a water bath until TLC (1:2 EtOAc:Heptane)
deemed the reaction complete. Afterwards, the reaction mixture was removed from the
water bath, 15 mL of water was added and the precipitate that formed was vacuum filtered.
The resulting solid was dissolved in a conical flask in 3 ml of hot ethanol and then poured
into 15 ml of water. After cooling the solution in an ice bath, the resulting precipitate was
vacuum filtered and left as such for 15 min to dry the crystals.
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Transcribed Image Text:ÓH (1) Ac20 / H3PO4 / 75°C ČH3 (4) Scheme 2: Acylation of (1) To a stirred solution of hydroxybenzoic acid 1 (1.0 g, 7.2 mmol) and acetic anhydride (2.5 mL, 26.4 mmol, 3.7 equivalents) was added 3 drops of concentrated phosphoric acid. The solution was stirred and warmed to 75°C on a water bath until TLC (1:2 EtOAc:Heptane) deemed the reaction complete. Afterwards, the reaction mixture was removed from the water bath, 15 mL of water was added and the precipitate that formed was vacuum filtered. The resulting solid was dissolved in a conical flask in 3 ml of hot ethanol and then poured into 15 ml of water. After cooling the solution in an ice bath, the resulting precipitate was vacuum filtered and left as such for 15 min to dry the crystals.
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