Sulfuric Acid → (3-(Phenylamino)phenyl)methanol

HRID 1462030

Reaction equation

HRID 1462030 reaction equation
[BH4-].[Na+].[NH:3]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13](OC)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.OS(O)(=O)=O>CO>[NH:3]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[CH2:13][OH:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 614856Methyl 3-(phenylamino)benzoateHCID 4311764Sodium borohydride

Product 1

HCID 12882229(3-(Phenylamino)phenyl)methanolYield 88.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under cooling with ice water, 7.2 g of sodium borohydride was gradually dropped into 4.5 g of methyl 3-anilinobenzoate dissolved in 20 ml of methanol. Then, the temperature was gradually raised and the reflux was carried out for 8 hours. The reaction mixture was poured into 10% H2SO4 aqueous solution which was being cooled with ice. 5.0 g of oily substance was obtained after the extraction with ether. In order to remove the remaining unreacted methyl ester, the hydrolysis was carried out with the addition of 5% KOH. The by-produced 3-anilinobenzoic acid was removed through alkali-washing to yield 3.5 g of 3-anilinobenzylalcohol.

Workup

  1. temperatureThen, the temperature was gradually raised
  2. temperaturewas being cooled with ice
  3. custom5.0 g of oily substance was obtained
  4. extractionafter the extraction with ether
  5. customIn order to remove the remaining unreacted methyl ester
  6. additionthe hydrolysis was carried out with the addition of 5% KOH
  7. customThe by-produced 3-anilinobenzoic acid was removed
  8. washthrough alkali-washing

Sources & evidence

ORD record
ord-2f9d6bb0fe3c4d1e9c5e74fe1037625e
Source dataset
uspto-grants-1984_07
Patent number
US04457940

Linked notes

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