Acetyl chloride → 4-(Acetoxymethyl)benzoic acid

HRID 2213703Notes

Reaction equation

HRID 2213703 reaction equation
C(N([CH2:6][CH3:7])CC)C.C(Cl)(=[O:10])C.[C:12]([O:15][CH2:16][CH3:17])(=[O:14])[CH3:13].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[C:12]([O:15][CH2:16][C:17]1[CH:7]=[CH:6][C:19]([C:20]([OH:10])=[O:21])=[CH:18][CH:22]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 70215904-(Acetoxymethyl)benzoic acid

Conditions

Temperature
0 °C

Procedure

Triethylamine (15.4 ml, 110.4 mmol) was added to a solution of aldehyde (2) (12.57 g, 02.4 mmol) in THF (50 ml) and cooled to 0° C. Acetyl chloride (7.91 g, 110.4 mmol ) was then gradually added over 25 minutes, and the mixture was then left to stir for two hours at room temperature. After one hour, ethyl acetate (200 ml) was added and the solution washed with sodium carbonate (100 ml), HCl (17%, 50 ml) and water (100 ml) respectively. The organic layer was then dried over sodium sulfate and the solvent removed under reduced pressure to give an oil which crystallised when cooled. Re-crystallisation in methanol-hexane gave light yellow crystals.

Workup

  1. waitthe mixture was then left
  2. waitAfter one hour
  3. washthe solution washed with sodium carbonate (100 ml), HCl (17%, 50 ml) and water (100 ml) respectively
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customto give an oil which
  7. customcrystallised when
  8. temperaturecooled
  9. customRe-crystallisation in methanol-hexane gave light yellow crystals

Sources & evidence

ORD record
ord-7be0acdcaffa4986b7db8d2a9c31e067
Source dataset
uspto-grants-2006_09
Patent number
US07105621B2

Reaction notes

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