4-Methyl-1-naphthoic acid
1-Acetyl-4-methylnaphthalene (40.66 g, 0.22 mol) was refluxed for 4.5 h with a hypochlorite solution prepared by dissolving NaOH (100g, 2.5mol) in water (135ml) and ice (500g), and bubbling CI2, into this solution until the increase in weight was 71 g (1 mol). The solution was allowed to cool and NaHSO, (60g) added in order to destroy excess hypochlorite. Concentrated HCI (75ml) was added to precipitate the 4- methyl-1-naphthoic acid. After recrystallization (95% EtOH) the acid (37.4g, 91%) was obtained
4-methyl-1-naphthoyl chloride
The acid chloride was prepared from 36.6g (180 mmol) of 4-methyl-1-naphthoic acid to which was added dropwise 300mL of thionyl chloride at a rate sufficient to maintain a steady evolution of gas. This solution was heated at reflux for 15min, cooled to ambient temperature and the excess thionyl chloride was removed in vacuo to give the acid chloride, which was used without further purification
1-Acetyl-4-methylnaphthalene (40.66 g, 0.22 mol) was refluxed for 4.5 h with a hypochlorite solution prepared by dissolving NaOH (100g, 2.5mol) in water (135ml) and ice (500g), and bubbling CI2, into this solution until the increase in weight was 71 g (1 mol). The solution was allowed to cool and NaHSO, (60g) added in order to destroy excess hypochlorite. Concentrated HCI (75ml) was added to precipitate the 4- methyl-1-naphthoic acid. After recrystallization (95% EtOH) the acid (37.4g, 91%) was obtained
4-methyl-1-naphthoyl chloride
The acid chloride was prepared from 36.6g (180 mmol) of 4-methyl-1-naphthoic acid to which was added dropwise 300mL of thionyl chloride at a rate sufficient to maintain a steady evolution of gas. This solution was heated at reflux for 15min, cooled to ambient temperature and the excess thionyl chloride was removed in vacuo to give the acid chloride, which was used without further purification