Acetic Acid → Benzenemethanol, 4-nitro-, 1-acetate

HRID 726480

Reaction equation

HRID 726480 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12](OC(=O)C)(=[O:14])[CH3:13].C(O)(=O)C>O>[C:12]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 12094Benzenemethanol, 4-nitro-, 1-acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.6 g (0.05 mol) of 4-nitrobenzyl alcohol, 4.7 ml (0.05 mol) of acetic anhydride and 5.8 ml (0.1 mol) of acetic acid were introduced into a round-bottomed flask and the mixture was heated at reflux for eight hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue was triturated in hexane, filtered and dried. 6.1 g (62%) of 4-nitrobenzyl acetate of melting point 77°-78° C. were recovered.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for eight hours
  3. extractionextracted with ethyl ether
  4. customthe organic phase decanted off
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was triturated in hexane
  8. filtrationfiltered
  9. customdried
  10. custom6.1 g (62%) of 4-nitrobenzyl acetate of melting point 77°-78° C. were recovered

Sources & evidence

ORD record
ord-688eb585bdcb494e85d1a56d24f7b9a6
Source dataset
uspto-grants-1998_01
Patent number
US05709867

Linked notes

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