[Cl:1]Cl.[C:3]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[OH:15])[CH:10]=[O:11])([CH3:6])([CH3:5])[CH3:4].O>C(O)(=O)C>[C:3]([C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([Cl:1])[C:14]=1[OH:15])[CH:10]=[O:11])([CH3:6])([CH3:4])[CH3:5]Chlorine gas was passed into a solution of 3-tert-butyl-4-hydroxybenzaldehyde (2.5 gm) in acetic acid (20 ml) for 1 hour. The solution was poured into water and the product collected. Recrystallisation from aqueous ethanol gave 3-tert-butyl-5-chloro-4-hydroxybenzaldehyde m.p. 123° C.
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