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

HRID 553281Notes

Reaction equation

HRID 553281 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>[CH3:1][O:15][C:14](=[O:16])[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]=[O:5])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 32834984-(Hydroxymethyl)phenylacetic acid

Product 1

HCID 19363032Methyl 2-(4-formylphenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (5 mL) was added cautiously to solution of (4-hydroxymethylphenyl)acetic acid (5.78 g) in methanol (200 mL), stirred for 18 hours and evaporated. The residue was dissolved in dichloromethane (100 mL) and treated with manganese (IV) oxide (29.47 g), stirred for 18 hours and filtered through Celite. The filter pad was washed with dichloromethane and the combined filtrates evaporated. Purification on silica, eluting with 20% diethyl ether in iso-hexane, afforded the subtitle compound as a white solid (3.60 g).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  3. additiontreated with manganese (IV) oxide (29.47 g)
  4. stirringstirred for 18 hours
  5. filtrationfiltered through Celite
  6. washThe filter pad was washed with dichloromethane
  7. customthe combined filtrates evaporated
  8. customPurification on silica
  9. washeluting with 20% diethyl ether in iso-hexane

Sources & evidence

ORD record
ord-073ae94e62a74aacb8593a2d4ed65733
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

Loading…