Acetyl chloride → 2-(Acetyloxy)-5-methylbenzoic acid

HRID 650217Notes

Reaction equation

HRID 650217 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:19]([O:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 69735-Methylsalicylic acidHCID 8471TriethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 232519582-(Acetyloxy)-5-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

1 g of 5-methylsalicylic acid (6.58 mmol) and 1.83 ml of tri-ethylamine (2 equivalents) were dissolved in 80 ml of ethyl acetate. At 0° C., 0.94 ml of acetyl chloride (2 equivalents) was added dropwise, and the mixture was then stirred at 23° C. for 1 h. The precipitated salts are [sic] filtered off. 100 ml of 1M HCl were added to the filtrate, which was then stirred overnight. A homogeneous solution formed, and it was adjusted to about pH 4 with saturated NaHCO3 solution. It was then extracted with chloroform, and the organic phase was washed with a little water and dried over MgSO4. The solvent was substantially removed, and the crude product was recrystallized from hexane/ethyl acetate.

Workup

  1. filtrationfiltered off
  2. addition100 ml of 1M HCl were added to the filtrate, which
  3. stirringwas then stirred overnight
  4. customA homogeneous solution formed
  5. extractionIt was then extracted with chloroform
  6. washthe organic phase was washed with a little water
  7. dry with materialdried over MgSO4
  8. customThe solvent was substantially removed
  9. customthe crude product was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-579bc849895b4a46bdb905776b48a2cb
Source dataset
uspto-grants-2001_08
Patent number
US06271345B1

Reaction notes

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