Acetyl chloride → HCID 10797860, compound

HRID 987838Notes

Reaction equation

HRID 987838 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].C([N:13](CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>C(OCC)(=O)C>[C:18]([O:10][C:3]1[C:4]([CH3:9])=[C:5]([C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[NH2:13])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 106982,4,6-Trimethylphenol

Product 1

HCID 10797860HCID 10797860, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4,6-trimethylphenol (10 g, 73.5 mmol) and triethylamine (11.1 g, 110.3 mmol) in ethyl acetate (200 mL) was added acetyl chloride (7.5 g, 95.6 mmol) dropwise at 0° C. The mixture was stirred overnight. The reaction was quenched with water and the organic layer was washed with 1 N HCl. The organic layer was dried and concentrated as usual. The residue was nitrated Example 14 (procedure B) and reduced as demonstrated for Example 14 (procedure C) to give 3-acetoxy-2,4,6-trimethylaniline.

Workup

  1. customThe reaction was quenched with water
  2. washthe organic layer was washed with 1 N HCl
  3. customThe organic layer was dried
  4. concentrationconcentrated as usual

Sources & evidence

ORD record
ord-bc979aa3a61a40ba86ab1ad6db23ea12
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

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