Acetyl chloride → Methyl 2-(4-formylphenyl)acetate

HRID 2205702Notes

Reaction equation

HRID 2205702 reaction equation
[C:1](Cl)(=O)C.[OH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1>CO.[O-2].[O-2].[Mn+4]>[CH:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH3:1])=[O:15])=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 32834984-(Hydroxymethyl)phenylacetic acid

Product 1

HCID 19363032Methyl 2-(4-formylphenyl)acetateYield 28%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

Acetyl chloride (5 mL) was added to an ice-cooled solution of 4-(hydroxymethyl)phenylacetic acid (5.78 g, 34.8 mmol) in methanol (200 mL). The reaction mixture allowed to warm to RT and stirred at this temperature for 42 hours. The solvent was evaporated at reduced pressure and the residue dissolved in DCM (100 mL). Manganese dioxide (29.47 g, 339 mmol) was added and the resultant suspension stirred at RT for 18 hours. The suspension was filtered through celite and the filter cake washed with further DCM. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0-25% ethyl acetate in iso-hexane to afford the title compound (1.72 g, 28%).

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. dissolutionthe residue dissolved in DCM (100 mL)
  3. filtrationThe suspension was filtered through celite
  4. washthe filter cake washed with further DCM
  5. customThe solvent was evaporated at reduced pressure
  6. customthe residue was purified by flash column chromatography
  7. washeluting with 0-25% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-dcce5b11146b45a5986144a96faa25d7
Source dataset
uspto-grants-2016_06
Patent number
US09371318B2

Reaction notes

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