Ethanol → HCID 15217556, compound

HRID 1741533Notes

Reaction equation

HRID 1741533 reaction equation
[CH2:1]([OH:3])C.C[O-].[Na+].C(OCC)=O.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=1[OH:19]>C(O)(=O)C.O>[OH:19][C:18]1[CH:17]=[C:16]([CH3:20])[CH:15]=[CH:14][C:13]=1[NH:12][CH:1]=[O:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 8025Ethyl formateHCID 760822-Amino-5-methylphenolHCID 10942334Sodium Methoxide

Product 1

HCID 15217556HCID 15217556, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 20 ml of ethanol, there were added under ice-cooling 4.83 g of sodium methoxide and 18.0 g of ethyl formate. Further, 10.0 g (81.3 mmol) of 6-amino-m-cresol was added thereto under ice-cooling. After putting back to room temperature, the solution was stirred under a nitrogen atmosphere for 1 hour. After the completion of the reaction, the reaction mixture was poured into 200 ml of water. The obtained solution was neutralized with glacial acetic acid, extracted with 300 ml of ethyl acetate, washed with 200 ml of 1N hydrochloric acid and 100 ml of a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous Glauber's salt. After distilling off the solvent under reduced pressure, 3.98 g (26.4 mmol) of N-(2-hydroxy-4-methylphenyl)formamide was obtained as a pale brown solid. The yield was 32%.

Workup

  1. temperatureunder ice-cooling
  2. customAfter putting back to room temperature
  3. customAfter the completion of the reaction
  4. extractionextracted with 300 ml of ethyl acetate
  5. washwashed with 200 ml of 1N hydrochloric acid and 100 ml of a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materialdried over anhydrous Glauber's salt
  7. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-a4c472da313f499d8d1bf2c3aa4f0467
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Reaction notes

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