Acetyl chloride → Methyl 2-(3-acetyl-4-hydroxyphenyl)propionate

HRID 26679Notes

Reaction equation

HRID 26679 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.[C:15](Cl)(=[O:17])[CH3:16].B(Cl)(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:15]([C:4]1[CH:5]=[C:6]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:8][C:3]=1[OH:2])(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 25135Boron TrichlorideHCID 12398855Methyl 2-(4-methoxyphenyl)propanoate

Product 1

HCID 21322000Methyl 2-(3-acetyl-4-hydroxyphenyl)propionate

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Titanium tetrachloride (82.3 mls) was added dropwise to a stirred solution of methyl 2-(4-methoxyphenyl)propionate (25 g) in dry dichloromethane (250 mls), cooled in an ice/salt-bath, at a rate sufficient to maintain the temperature between -10° C. and -5° C. The mixture was stirred for 10 minutes and acetyl chloride (10 g) was added dropwise at a rate sufficient to maintain the temperature below 0° C. The solution was stirred at -5° C. for 11/2 hours when boron trichloride (15 mls) was added. Stirring was continued for 1/2 hour at +3° C. before pouring on to crushed ice/concentrated hydrochloric and separating the two phases. The aqueous phase was extracted with ether (3x) and the combined organic extracts were washed with saturated sodium bicarbonate solution, saturated brine solution, and dried over anhydrous magnesium sulphate. Evaporation of the solvent yielded the crude product as a pale yellow oil. Vacuum distillation furnished a pale yellow oil bp 120°-125° C./0.15 mm (16.2 g; 59%)

Workup

  1. temperaturecooled in an ice/salt-bath, at a rate sufficient
  2. temperatureto maintain the temperature between -10° C. and -5° C
  3. temperatureto maintain the temperature below 0° C
  4. additionwas added
  5. stirringStirring
  6. waitwas continued for 1/2 hour at +3° C.
  7. additionbefore pouring on
  8. customto crushed ice/
  9. concentrationconcentrated hydrochloric
  10. customseparating the two phases
  11. extractionThe aqueous phase was extracted with ether (3x)
  12. washthe combined organic extracts were washed with saturated sodium bicarbonate solution, saturated brine solution
  13. dry with materialdried over anhydrous magnesium sulphate
  14. customEvaporation of the solvent
  15. customyielded the crude product as a pale yellow oil
  16. distillationVacuum distillation

Sources & evidence

ORD record
ord-ab2ce73424b541b4a81672a916ba67f8
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Reaction notes

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