HCID 13371463, compound → 2-((4-Hydroxyphenyl)amino)-5-methoxybenzenemethanol

HRID 2413270Notes

Reaction equation

HRID 2413270 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[CH2:24][OH:25])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[CH2:24][OH:25])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 13371463HCID 13371463, compound

Product 1

HCID 1245222-((4-Hydroxyphenyl)amino)-5-methoxybenzenemethanolYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2.41 g of 2-(4-benzyloxyphenylamino)-5-methoxybenzenemethanol in 200 ml of ethanol was added 60 mg of 10% palladium-on-carbon catalyst, and the mixture was hydrogenated on a Parr apparatus at room temperature and an initial pressure of 34 psi for 73 minutes. The reaction mixture was filtered and concentrated in vacuo to a volume of about 10 ml. Toluene (40 ml) was added and about half of the volume evaporated. The solution was cooled and crystallization induced. The solid product was collected and dried to give 1.3 g of 2-(4-hydroxyphenylamino)-5-methoxybenzenemethanol, pale lavender powder, m.p. 96.5°-97° C.

Workup

  1. customwas hydrogenated on a Parr apparatus at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo to a volume of about 10 ml
  4. additionToluene (40 ml) was added and about half of the volume
  5. customevaporated
  6. temperatureThe solution was cooled
  7. customcrystallization
  8. customThe solid product was collected
  9. customdried

Sources & evidence

ORD record
ord-0542a6d335874029a41e02ba27e0b2a0
Source dataset
uspto-grants-1985_01
Patent number
US04496590

Reaction notes

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