Acetyl chloride → Methyl 3-hydroxy-4-nitrobenzoate

HRID 615847Notes

Reaction equation

HRID 615847 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 recrystalized 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 recrystalized from methanol (150 ml)

Sources & evidence

ORD record
ord-802b356c9f844fbdb0b2893a78ec1ac7
Source dataset
uspto-grants-1985_02
Patent number
US04501692

Reaction notes

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