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

HRID 382915Notes

Reaction equation

HRID 382915 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

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 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

46.6 g of the benzyl 4-(4-nitro-3-benzyloxyphenoxy)benzoate (0.11 mol) prepared as described in Example 4 are dissolved in 500 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), 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-1a11319cbc2d46bba96ed07eba648384
Source dataset
uspto-grants-2001_10
Patent number
US06310238B1

Reaction notes

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