1-Naphthoic acid → 1-Naphthalenecarbonyl chloride
Reaction equation
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>>[C:1]1([C:11]([Cl:16])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 1.03 g of 1-naphthoic acid and 4.86 g of thionyl chloride was stirred at 50° C. for 2 hours. An excess of thionyl chloride was removed under reduced pressure to give 1-naphthoyl chloride. A solution of 1-naphthoyl chloride in 10 ml of benzene was added dropwise to mixture of 1.06 g of N-methyl-4-tertbutylbenzylamine, 2 ml of pyridine and 10 ml of dry benzene and was stirred for 5 hours. The resultant was poured into water and extracted with benzene, and the benzene solution was washed successively with 3% aqueous solution of sodium bicarbonate, 3% hydrochloric acid and water, and then dried over anhydrous sodium sulfate. Oily product (1.74 g, amide) was obtained by distilling away benzene and was crystallized by leaving as it was. Melting point: 106° to 108° C. (recrystallized from hexane/benzene)
Workup
- customAn excess of thionyl chloride was removed under reduced pressure
Sources & evidence
- ORD record
- ord-23ab26cbbc564902bba0cbbf0f89fabf
- Source dataset
- uspto-grants-1994_11
- Patent number
- USRE034770
Reaction notes
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