Methanol → Benzoic acid, 3-methyl-2-nitro-, methyl ester

HRID 1263171Notes

Reaction equation

HRID 1263171 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](Cl)=[O:9])[C:3]=1[N+:11]([O-:13])=[O:12].C(Cl)Cl.[CH3:17][OH:18].C(N(CC)CC)C>C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:18][CH3:17])=[O:9])[C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 8471TriethylamineHCID 2671613-methyl-2-nitrobenzoyl chloride

Product 1

HCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl esterYield 93.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In this example a solution containing 1.002 mole of 2-methyl-6-chlorocarbonyl-nitrobenzene in 200 ml of ethyl ether and a small amount of methylene chloride was added to mixture containing 1.5 mole (60.8 ml) of methanol 1.002 mole (139.7 ml) of triethylamine and 200 ml of ethyl ether at about 0° C. The resulting mixture was stirred for one hour and then allowed to stand overnight. The mixture was then filtered and the filtrate washed with dilute aqueous acid and then washed with an aqueous sodium bicarbonate solution. The washed filtrate was dried and evaporated affording 183.3 g of the title product.

Workup

  1. waitto stand overnight
  2. filtrationThe mixture was then filtered
  3. washthe filtrate washed with dilute aqueous acid
  4. washwashed with an aqueous sodium bicarbonate solution
  5. customThe washed filtrate was dried
  6. customevaporated

Sources & evidence

ORD record
ord-ffea242ab0b44711acfc65ce61ded6d5
Source dataset
uspto-grants-1984_06
Patent number
US04456471

Reaction notes

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