24.6 Sources of Phenols

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1 24.6 Sources of Phenols Phenol is an important industrial chemical. Major use is in phenolic resins for adhesives and plastics. Annual U.S. production is about 4 billion pounds per year.

2 Industrial Preparations of Phenol S 3 Cl C(C 3 ) 2 1. Na heat Na heat S 4

3 Laboratory Synthesis of Phenols from arylamines via diazonium ions 2 N N 2 1. NaN 2, 2 S 4, , heat 2 N (81-86%) 86%)

4 24.7 Naturally ccurring Phenols Many phenols occur naturally

5 Example: Thymol C 3 C(C 3 ) 2 Thymol (major constituent of oil of thyme)

6 Example: 2,5-Dichlorophenol Cl Cl 2,5-Dichlorophenol (from defensive secretion of a species of grasshopper)

7 24.8 Reactions of Phenols: Electrophilic Aromatic Substitution ydroxyl group strongly activates the ring toward electrophilic aromatic substitution

8 Electrophilic Aromatic Substitution in Phenols alogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation

9 alogenation + Br 2 ClC 2 C 2 Cl 0 C Br (93%) monohalogenation in nonpolar solvent (1,2-dichloroethane)

10 alogenation F + 3Br C Br Br F multiple halogenation in polar solvent (water) Br (95%)

11 Electrophilic Aromatic Substitution in Phenols alogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation

12 Nitration N 3 N 2 C 3 acetic acid 5 C C 3 group controls regiochemistry (73-77%) 77%)

13 Electrophilic Aromatic Substitution in Phenols alogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation

14 Nitrosation N NaN 2 2 S 4, 2 0 C only strongly activated rings undergo nitrosation when treated with nitrous acid (99%)

15 Electrophilic Aromatic Substitution in Phenols alogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation

16 Sulfonation 3 C C 3 2 S 4 3 C C C group controls regiochemistry S 3 (69%)

17 Electrophilic Aromatic Substitution in Phenols alogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation

18 Friedel-Crafts Alkylation C 3 (C 3 ) 3 C C 3 3 P 4 60 C 3 C C C 3 (C 3 ) 3 C reacts with 3 P 4 to give (C 3 ) 3 C + C 3 (63%)

19 Electrophilic Aromatic Substitution in Phenols alogenation Nitration Nitrosation Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation

20 24.9 Acylation of Phenols Acylation can take place either on the ring by electrophilic aromatic substitution or on oxygen by nucleophilic acyl substitution

21 Friedel-Crafts Acylation C 3 CCl AlCl 3 + ortho isomer under Friedel-Crafts conditions, acylation of the ring occurs (C-acylation) C (74%) C 3 (16%)

22 -Acylation C(C 2 ) 6 C 3 + C 3 (C 2 ) 6 CCl (95%) in the absence of AlCl 3, acylation of the hydroxyl group occurs (-acylation)

23 C(C 2 ) 6 C 3 - versus C-AcylationC AlCl 3 formed faster C C 3 more stable -Acylation is kinetically controlled process; C-acylation C is thermodynamically controlled AlCl 3 catalyzes the conversion of the aryl ester to the aryl alkyl ketones; this is called the Fries rearrangement

24 24.10 Carboxylation of Phenols Aspirin and the Kolbe-Schmitt Reaction CC 3 C

25 Aspirin is prepared from salicylic acid C C 3 CCC 3 2 S 4 CC 3 C how is salicylic acid prepared?

26 Preparation of Salicylic Acid Na C C, 100 atm CNa called the Kolbe-Schmitt reaction acidification converts the sodium salt shown above to salicylic acid

27 What Drives the Reaction? acid-base considerations provide an explanation: stronger base on left; weaker base on right stronger base: pk a of conjugate acid = 10 + C 2 C weaker base: pk a of conjugate acid = 3

28 Preparation of Salicylic Acid Na C C, 100 atm CNa how does carbon-carbon bond form? recall electron delocalization in phenoxide ion negative charge shared by oxygen and by the ring carbons that are ortho and para to oxygen

29

30 Mechanism of ortho Carboxylation C C

31 Mechanism of ortho Carboxylation C C C

32 Why ortho? Why not para? C C

33 Why ortho? Why not para? C weaker base: pk a of conjugate acid = 3 C stronger base: pk a of conjugate acid = 4.5

34 Intramolecular ydrogen Bonding in Salicylate Ion C ydrogen bonding between carboxylate and hydroxyl group stabilizes salicylate ion. Salicylate is less basic than para isomer and predominates under conditions of thermodynamic control.

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