Acetic Acid → 6-(4-Hydroxyphenyl)-2-naphthalenecarboxylic acid
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]([OH:21])=[O:20])[CH:15]=3)[CH:10]=2)=[CH:5][CH:4]=1.C(O)(=O)C.C(OC(=O)C)(=O)C.Br>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]([OH:21])=[O:20])[CH:15]=3)[CH:10]=2)=[CH:7][CH:8]=1Participants
Procedure
Into a four-necked flask equipped with a stirring rod, dropping funnel, reflux condenser and thermometer was charged 0.63 g (0.0023 mol) of 2-(4'-methoxyphenyl)naphthalene-6-carboxylic acid of Example 9. To the compound were added 50 ml of acetic acid, 30 ml of acetic anhydride and 15 ml of 48% hydrobromic acid. The reaction was continued for 10 hours while the mixture was being heated with stirring, thereby obtaining clear solution. When 50 ml of water was added to the reaction solution, white precipitate was obtained. The precipitate was separated from the mixture by filtration, and then dried to obtain 0.5 g of 2-(4'-hydroxyphenyl)naphthalene-6-carboxylic acid. The yield of the product was 82 mol % on the basis of 2-(4'-methoxyphenyl)naphthalene-6-carboxylic acid used. The purity of the produce was 98%.
Workup
- customInto a four-necked flask equipped with a stirring rod
- temperaturereflux condenser
- temperaturewas being heated
- customobtaining clear solution
- customwhite precipitate was obtained
- customThe precipitate was separated from the mixture by filtration
- customdried
Sources & evidence
- ORD record
- ord-369699fa892e4009a68ba0d2e2780ee1
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05151549
Reaction notes
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