Hydrochloric Acid → (2,6-Dimethyl-3-nitrophenyl)methyl acetate

HRID 1995123Notes

Reaction equation

HRID 1995123 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[C:3]=1[CH2:12][OH:13].N1C=CC=CC=1.[C:20](Cl)(=[O:22])[CH3:21].Cl>C1(C)C=CC=CC=1>[C:20]([O:13][CH2:12][C:3]1[C:4]([CH3:11])=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 10487641(2,6-Dimethyl-3-nitrophenyl)methanol

Product 1

HCID 10537042(2,6-Dimethyl-3-nitrophenyl)methyl acetateYield 75.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2,6-dimethyl-3-nitrobenzene-1-methanol (51.3 g, 0.283 mole) and 25 ml of pyridine in 350 ml of toluene was warmed to 70°. During a ten minute period, acetyl chloride (22.2 g, 0.283 mole) was added to the reaction mixture. The reaction mixture was heated at 85° for 21/2 hours, then poured over 300 g of ice, and 100 ml of a 4 N hydrochloric acid solution was added thereto. The organic phase was separated and washed with 100 ml of aqueous 2 N hydrochloric acid, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed from the filtrate under reduced pressure to give (2,6-dimethyl-3-nitrophenyl)methyl acetate (47.5 g) as an oil.

Workup

  1. temperatureThe reaction mixture was heated at 85° for 21/2 hours
  2. additionwas added
  3. customThe organic phase was separated
  4. washwashed with 100 ml of aqueous 2 N hydrochloric acid
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-f2ec323373c34d60b76391797d1784bc
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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