[4-(4-Nitrophenoxy)phenyl]acetic acid → HCID 20392568, compound

HRID 1863265Notes

Reaction equation

HRID 1863265 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 10858649[4-(4-Nitrophenoxy)phenyl]acetic acid

Product 1

HCID 20392568HCID 20392568, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of 13.65 g of [p-(p-nitrophenoxy)phenyl]acetic acid in 100 ml of ethanol is added 130 mg of platinum oxide. The mixture is shaken under 45 lb hydrogen pressure in a Parr shaker. After 2 hours, a thick white solid precipitates. The mixture is filtered, and 200 mg of fresh platinum oxide is added to the filtrate which is subjected to the reducing conditions. After an additional hour, the mixture is filtered and washed with cold ethanol. The combined solids are dissolved in hot methanol and filtered. Water is added to the filtrate to afford 4.9 g of a brown solid. A portion is recrystallized from methanol to yield the product as cream colored crystals, mp 172° C. (dec.).

Workup

  1. customa thick white solid precipitates
  2. filtrationThe mixture is filtered
  3. addition200 mg of fresh platinum oxide is added to the filtrate which
  4. waitAfter an additional hour
  5. filtrationthe mixture is filtered
  6. washwashed with cold ethanol
  7. dissolutionThe combined solids are dissolved in hot methanol
  8. filtrationfiltered
  9. additionWater is added to the filtrate

Sources & evidence

ORD record
ord-56fe100e97ed4591ac844901abce88d9
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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