Acetyl chloride → Methyl 3-hydroxy-4-nitrobenzoate

HRID 1577282Notes

Reaction equation

HRID 1577282 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[C:14](Cl)(=O)C>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH3:14])=[O:6]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxy-4-nitrobenzoic acid (I) (100.3 g, 95% pure, 0.53 mole) was added to methanol (1250 ml) to which had been added acetyl chloride (25 ml). The solid dissolved over a period of two days. After six days, the solution was filtered to remove undissolved impurities. The crude ester was obtained by evaporation of the solution. Several crops of crystals were taken, the last from a 50 ml volume. The combined crops were recrystallized from methanol (150 ml). Two crops of the ester (II) as yellow-brown crystals, m.p. 89°-91°, (98.7 g, 0.50 mole) were obtained.

Workup

  1. dissolutionThe solid dissolved over a period of two days
  2. filtrationthe solution was filtered
  3. customto remove undissolved impurities
  4. customThe crude ester was obtained by evaporation of the solution
  5. customThe combined crops were recrystallized from methanol (150 ml)

Sources & evidence

ORD record
ord-82ee7f3ac3d340ec8df7de94f02804e6
Source dataset
uspto-grants-1981_09
Patent number
US04287300

Reaction notes

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