Succinic anhydride → 4-[4-(Octyloxy)phenyl]-4-oxobutanoic acid

HRID 542389Notes

Reaction equation

HRID 542389 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:22])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 74558Octyl phenyl etherHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27752384-[4-(Octyloxy)phenyl]-4-oxobutanoic acidYield 53.2%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
50 °C

Procedure

n-Octyloxybenzene (301 g, 1.46 mol), succinic anhydride (146.8 g, 1.468 mol) and carbon disulfide (1.3 l) were agitated at room temperature, followed by portion-wise feeding anhydrous aluminum chloride (392 g, 2.94 mol), further agitating the mixture at 50° C. for 4 hours after the reaction became quiet, cooling the mixture down to room temperature, adding it to ice (2 Kg), distilling off carbon disulfide, collecting solids, adding toluene (1 l), distilling off water on heating, filtering while hot, and distilling off toluene under reduced pressure to obtain oily β-(p-octyloxybenzoyl)-propionic acid (238 g, yield 53%).

Workup

  1. temperaturecooling the mixture down to room temperature
  2. distillationdistilling off carbon disulfide
  3. customcollecting solids
  4. additionadding toluene (1 l)
  5. distillationdistilling off water
  6. temperatureon heating
  7. filtrationfiltering while hot, and
  8. distillationdistilling off toluene under reduced pressure

Sources & evidence

ORD record
ord-cdfcc2e536cd4e05bca7da159b0aca0d
Source dataset
uspto-grants-1987_04
Patent number
US04657695

Reaction notes

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