Ethanol → Ethyl 3-hydroxy-5-nitro-4-phenylbenzoate

HRID 1605550Notes

Reaction equation

HRID 1605550 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:25](O)[CH3:26]>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([O:7][CH2:25][CH3:26])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 215468503-Hydroxy-5-nitro-4-phenylbenzoic acid

Product 1

HCID 21546856Ethyl 3-hydroxy-5-nitro-4-phenylbenzoate

Procedure

A mixture of 3-hydroxy-5-nitro-4-phenylbenzoic acid (22 g; prepared as in Example 2, step B), conc. sulfuric acid (10 ml) and ethanol (400 ml) is refluxed for 20 hours. The resulting solution is concentrated in vacuo to about 100 ml and is then diluted with water (about 300 ml). The separated ethyl 3-hydroxy-5-nitro-4-phenylbenzoate is collected by filtration, washed with water and dried. After recrystallization from carbon tetrachloride, the ester is obtained with a melting point of 128°-130° C.

Workup

  1. temperatureis refluxed for 20 hours
  2. concentrationThe resulting solution is concentrated in vacuo to about 100 ml
  3. additionis then diluted with water (about 300 ml)
  4. filtrationThe separated ethyl 3-hydroxy-5-nitro-4-phenylbenzoate is collected by filtration
  5. washwashed with water
  6. customdried
  7. customAfter recrystallization from carbon tetrachloride

Sources & evidence

ORD record
ord-5bb7d02f634e487197aeaecae7bac572
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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