PHENOLS 679 (d) Friedel-Crafts acylation occurs ortho to the hydroxyl group CCHCH Ch3CHaCCI H3 p-Cresol 1-(2-Hydroxy-5-methylpher 24.7(b) The hydroxyl group of 2-naphthol is converted to the corresponding acetate ester OH OCCH CH3COCCH3 CH CONa 2-Naphthol Acetic anhydride 2-Naphthyl acetate Sodium acetate (c) Benzoyl chloride acylates the hydroxyl group of phenol CCI t HCl Phenol Benzoyl chloride Phenyl benzoate 24.8 Epoxides are sensitive to nucleophilic ring-opening reactions. Phenoxide ion attacks the less hin- dered carbon to yield l-phenoxy-2-propanol ④“政mm OCH-CHCH Phenoxide ion 1, 2-Epoxypropane l-Phenoxy-2-propanol 24.9 The aryl halide must be one that is reactive toward nucleophilic aromatic substitution by the addition-elimination mechanism. p-Flt trobenzene is far more reactive than fluorobenzene The reaction shown yields p-nitrophenyl phenyl ether in 92%o yield. p-Nitrophenyl phenyl ether 24.10 Substituted allyl aryl ethers undergo a Claisen rearrangement similar to the reaction described in text Section 24.13 for allyl phenyl ether. 2-Butenyl phenyl ether rearranges on heating to give o-(1 meth oH enolization 2-Butenyl phenyl Methyl-2 Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website(d ) Friedel–Crafts acylation occurs ortho to the hydroxyl group. 24.7 (b) The hydroxyl group of 2-naphthol is converted to the corresponding acetate ester. (c) Benzoyl chloride acylates the hydroxyl group of phenol. 24.8 Epoxides are sensitive to nucleophilic ring-opening reactions. Phenoxide ion attacks the less hin￾dered carbon to yield 1-phenoxy-2-propanol. 24.9 The aryl halide must be one that is reactive toward nucleophilic aromatic substitution by the addition–elimination mechanism. p-Fluoronitrobenzene is far more reactive than fluorobenzene. The reaction shown yields p-nitrophenyl phenyl ether in 92% yield. 24.10 Substituted allyl aryl ethers undergo a Claisen rearrangement similar to the reaction described in text Section 24.13 for allyl phenyl ether. 2-Butenyl phenyl ether rearranges on heating to give o-(1- methyl-2-propenyl)phenol. O H OH o-(1-Methyl-2-propenyl)- phenol rearrangement enolization 2-Butenyl phenyl ether O OK  Potassium phenoxide F NO2 p-Fluoronitrobenzene O NO2 p-Nitrophenyl phenyl ether 150C OCH2CHCH3 OH 1-Phenoxy-2-propanol O Phenoxide ion HO, H2O 1,2-Epoxypropane H2C O CHCH3   Phenyl benzoate OC O Phenol OH Benzoyl chloride O CCl Hydrogen chloride HCl   NaOH 2-Naphthyl acetate OCCH3 O 2-Naphthol OH Sodium acetate CH3CONa O Acetic anhydride CH3COCCH3 O O AlCl3 OH CH3 O  CH3CH2CCl p-Cresol Propanoyl chloride CCH2CH3 OH CH3 O 1-(2-Hydroxy-5-methylphenyl)- 1-propanone (isolated yield, 87%) PHENOLS 679 Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website