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Benzyl 4-(4-nitro-3-benzyloxyphenoxy)benzoate → 4-(4-Amino-3-hydroxyphenoxy)benzoic acid

HRID 2304998
Notes
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Reaction equation

HRID 2304998 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 18459341Benzyl 4-(4-nitro-3-benzyloxyphenoxy)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 177867174-(4-Amino-3-hydroxyphenoxy)benzoic acidYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

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

  1. additionare added to the solution
  2. customat room temperature
  3. customthe reaction is terminated after 3 days
  4. customThe pale violet solution is evaporated to half in a rotary evaporator
  5. waitleft
  6. customthe reaction product precipitates out in crystalline form
  7. customThe reaction product is then separated off
  8. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  9. customdrying cabinet (yield: 93%)

Sources & evidence

ORD record
ord-62960e0d643c45b88e076a313c51a10b
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06437178B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes