Benzyl 4-(4-nitro-3-benzyloxyphenoxy)benzoate → 4-(4-Amino-3-hydroxyphenoxy)benzoic acid
Reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([O:15]CC3C=CC=CC=3)=[O:14])=[CH:11][CH:10]=2)=[CH:6][C:5]=1[O:27]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[CH:6][C:5]=1[OH:27]Participants
Procedure
46.6 g of the benzyl 4-(4-nitro-3-benzyloxyphenoxy)benzoate prepared as described in Example 4 (0.11 mol) are dissolved in 500 ml of a mixture of tetrahydrofuran and ethyl acetate, and 5 g of Pd/C (palladium/carbon) are added to the solution. The mixture is then hydrogenated using hydrogen at a pressure of 1 bar at room temperature in an autoclave with vigorous stirring; the reaction is terminated after 3 days. The pale violet solution is evaporated to half in a rotary evaporator and left to stand overnight at room temperature, during which the reaction product precipitates out in crystalline form. The reaction product is then separated off and dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 93%).
Workup
- additionare added to the solution
- customat room temperature
- customthe reaction is terminated after 3 days
- customThe pale violet solution is evaporated to half in a rotary evaporator
- waitleft
- customthe reaction product precipitates out in crystalline form
- customThe reaction product is then separated off
- customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
- customdrying cabinet (yield: 93%)
Sources & evidence
- ORD record
- ord-62960e0d643c45b88e076a313c51a10b
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06437178B2
Reaction notes
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