Nitric Acid → 7-Nitro-1,2,3,4-tetrahydro-5-naphthoic acid
Reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:14]([O-])([OH:16])=[O:15]>>[N+:14]([C:3]1[CH:2]=[C:1]([C:11]([OH:13])=[O:12])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1)([O-:16])=[O:15]Participants
3
Conditions
- Temperature
- 2 °C
Procedure
Fuming red nitric acid (150 ml.) was cooled to 2° C. and 27.3 g. of 5,6,7,8-tetrahydronaphthalene-1-carboxylic acid was added portionwise over 0.5 hour with stirring maintaining the temperature at 2°-6° C. After another 45 minutes at about 5° C. the mixture was poured into 1500 ml. of crushed ice. The precipitate was collected and washed well with 5 × 500 ml. portions of water. The dried precipitate was heated with about 200 ml. of benzene. The insoluble material was collected and recrystallized from ethyl acetate to give 3-nitro-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid, m.p. 209°-212° C.