From Cumene: $\text{Cumene} \xrightarrow{(\text{i}) \text{O}_2 (\text{ii}) \text{H}^+} \text{Phenol} + \text{Acetone}$

Acidity: $\text{ROH} + \text{Na} \rightarrow \text{RONa} + 1/2 \text{H}_2$
Esterification: $\text{ROH} + \text{R'COOH} \xrightarrow{\text{Conc. H}_2\text{SO}_4} \text{R'COOR} + \text{H}_2\text{O}$
Dehydration: $\text{R-CH}_2\text{CH}_2\text{OH} \xrightarrow{\text{Conc. H}_2\text{SO}_4, 443K} \text{R-CH=CH}_2 + \text{H}_2\text{O}$
Oxidation:
- Primary alcohol: $\text{RCH}_2\text{OH} \xrightarrow{\text{PCC}} \text{RCHO}$ (aldehyde)
- Primary alcohol: $\text{RCH}_2\text{OH} \xrightarrow{\text{CrO}_3 \text{ or } \text{KMnO}_4} \text{RCOOH}$ (carboxylic acid)
- Secondary alcohol: $\text{RCH(OH)R'} \xrightarrow{\text{CrO}_3} \text{RCOR'}$ (ketone)
- Tertiary alcohol: No oxidation under mild conditions.
Reaction with HX: $\text{ROH} + \text{HX} \rightarrow \text{RX} + \text{H}_2\text{O}$
Reaction with $\text{PCl}_3, \text{PCl}_5, \text{SOCl}_2$: (See Haloalkanes preparation)

Acidity: $\text{Phenol} + \text{NaOH} \rightarrow \text{Sodium Phenoxide} + \text{H}_2\text{O}$
Electrophilic Substitution: (Ortho/Para directing, activating)
- Nitration: $\text{Phenol} \xrightarrow{\text{Dil. HNO}_3} \text{o-/p-Nitrophenol}$
- Nitration: $\text{Phenol} \xrightarrow{\text{Conc. HNO}_3/\text{H}_2\text{SO}_4} \text{Picric acid (2,4,6-trinitrophenol)}$
- Bromination: $\text{Phenol} \xrightarrow{\text{Br}_2/\text{CS}_2} \text{o-/p-Bromophenol}$
- Bromination: $\text{Phenol} \xrightarrow{\text{Br}_2/\text{H}_2\text{O}} \text{2,4,6-Tribromophenol}$
- Kolbe's Reaction: $\text{Sodium Phenoxide} \xrightarrow{(\text{i}) \text{CO}_2, 400K, 4-7 atm (\text{ii}) \text{H}^+} \text{Salicylic acid}$
- Reimer-Tiemann Reaction: $\text{Phenol} \xrightarrow{(\text{i}) \text{CHCl}_3/\text{NaOH} (\text{ii}) \text{H}^+} \text{Salicylaldehyde}$
Reaction with Zinc Dust: $\text{Phenol} \xrightarrow{\text{Zn dust}} \text{Benzene}$
Oxidation: $\text{Phenol} \xrightarrow{\text{Na}_2\text{Cr}_2\text{O}_7/\text{H}_2\text{SO}_4} \text{Benzoquinone}$

From Alcohols (Dehydration): $2\text{ROH} \xrightarrow{\text{Conc. H}_2\text{SO}_4, 413K} \text{R-O-R} + \text{H}_2\text{O}$ (Symmetric ethers)
Williamson Synthesis: $\text{R-X} + \text{NaOR'} \rightarrow \text{R-O-R'} + \text{NaX}$ (Symmetric and unsymmetric ethers)

Cleavage by HX: $\text{R-O-R'} + \text{HX} \rightarrow \text{ROH} + \text{R'X}$ (order of reactivity $\text{HI} > \text{HBr} > \text{HCl}$)
Electrophilic Substitution (in aromatic ethers): (Ortho/Para directing, activating)
- Halogenation: $\text{Methoxybenzene} + \text{Br}_2/\text{CH}_3\text{COOH} \rightarrow \text{o-/p-Bromoanisole}$
- Nitration: $\text{Methoxybenzene} + \text{HNO}_3/\text{H}_2\text{SO}_4 \rightarrow \text{o-/p-Nitroanisole}$
- Friedel-Crafts Alkylation: $\text{Methoxybenzene} + \text{CH}_3\text{Cl} \xrightarrow{\text{Anhy. AlCl}_3} \text{o-/p-Methylanisole}$
- Friedel-Crafts Acylation: $\text{Methoxybenzene} + \text{CH}_3\text{COCl} \xrightarrow{\text{Anhy. AlCl}_3} \text{o-/p-Methoxyacetophenone}$