Acetyl chloride → 2-Formyl-5-methylphenyl acetate

HRID 1773211Notes

Reaction equation

HRID 1773211 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](Cl)(=[O:13])[CH3:12]>C(Cl)Cl>[C:11]([O:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 612002-Hydroxy-4-methylbenzaldehyde

Product 1

HCID 538517102-Formyl-5-methylphenyl acetateYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a 0-5° C. solution of 2-hydroxy-4-methylbenzaldehyde (15 g, 110 mmol) in 250 mL of DCM was added TEA (30.7 ml, 220 mmol) followed by dropwise addition of acetyl chloride (8.65 g, 110 mmol) over 15 min. The reaction was stirred at 0-5° C. for 30 min. The reaction mixture was concentrated under reduced pressure. To this residue 100 mL of 1N HCl was added. The crude mixture was extracted with EtOAc×2. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give a yellow oil, 2-formyl-5-methylphenyl acetate (18 g). 1H NMR (400 MHz, DMSO-d6) δ 2.34 (s, 3H), 2.40 (s, 3H), 7.13 (s, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.80 (d, J=7.8 Hz, 1H), 10.01 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo this residue 100 mL of 1N HCl was added
  3. extractionThe crude mixture was extracted with EtOAc×2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2361d1ba117a4316a9b84bf4c6474b60
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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