Ethanol → 3-(3,5-Di-tertiary-butyl-4-hydroxyanilino)phenoxyacetic acid

HRID 2226313Notes

Reaction equation

HRID 2226313 reaction equation
[C:1]([C:5]1[C:6](=[O:27])[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:8][C:9](=[N:11][C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=2)[O:15][CH2:16][C:17]([OH:19])=[O:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C>[Pd].C1C=CC=CC=1>[C:23]([C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:27])[NH:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[O:15][CH2:16][C:17]([OH:19])=[O:18])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 702EthanolHCID 224015713-(2,6-Di-tertiary-butyl-cyclohexadienon-4-ylideneamino)phenoxyacetic acid

Product 1

HCID 224015693-(3,5-Di-tertiary-butyl-4-hydroxyanilino)phenoxyacetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 5.0 g of 3-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenoxyacetic acid, 250 ml of ethanol and 10 mg of 5% palladium on charcoal catalyst was placed on a Paar apparatus. Hydrogenation was complete after five hours. The reaction mixture was filtered to remove the catalyst and the filtrate was evaporated to give a thick brown oil. The oil was dissolved in 20 ml of benzene, filtered, diluted with 20 ml of cyclohexane and 10 ml of hexane, and chilled to give 1.4 g of light tan crystalline 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)phenoxyacetic acid, m.p. 127°-127.5° C. Analysis: Calculated for C22H29NO4 : % C, 71.1; % H, 7.9; % N, 3.8; Found: % C, 70.3; % H, 7.6; % N, 3.7.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. customthe filtrate was evaporated
  4. customto give a thick brown oil
  5. filtrationfiltered
  6. additiondiluted with 20 ml of cyclohexane and 10 ml of hexane
  7. temperaturechilled

Sources & evidence

ORD record
ord-82a3badcb10b49c691dfd69a8461047f
Source dataset
uspto-grants-1994_09
Patent number
US05347036

Reaction notes

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