Reaction #54891

ord-ebd06921660b4c5b907ee6c283683948

Reaction equation

CCCCCC(O)CCCC(CCCc1ccc(C(=O)O)cc1)C(C)=O
4-(4-acetyl-8-hydroxytridecyl)benzoic acid
CC(=O)OC(C)=O
acetic anhydride
→
CCCCCC(CCCC(CCCc1ccc(C(=O)O)cc1)C(C)=O)OC(C)=O
crude product
CCCCCC(CCCC(CCCc1ccc(C(=O)O)cc1)C(C)=O)OC(C)=O
4-(4-Acetyl-8-acetoxytridecyl)benzoic Acid

Reactants

CCCCCC(O)CCCC(CCCc1ccc(C(=O)O)cc1)C(C)=O
4-(4-acetyl-8-hydroxytridecyl)benzoic acid
CC(=O)OC(C)=O
acetic anhydride

Reagents

None

Solvents

CCOCC
ethyl ether

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture is then cooled
  2. 2
    workup.DISSOLUTIONdissolved in 80 ml
  3. 3
    ExtractionThe solution is extracted with an ice-cold solution of 8 g
  4. 4
    OtherThe basic solution is separated
  5. 5
    Washwashed with water
  6. 6
    Dryingdried over sodium sulfate
  7. 7
    OtherThe ether is evaporated

Procedure

A mixture of 4-(4-acetyl-8-hydroxytridecyl)benzoic acid (9.0 g., 0.025 mole) and acetic anhydride (6.1 g., 0.06 mole) is heated at 60° C. for 18 hours. The mixture is then cooled and dissolved in 80 ml. ethyl ether. The solution is extracted with an ice-cold solution of 8 g. sodium hydroxide in 150 ml. water. The basic solution is separated and acidified with concentrated hydrochloric acid. The oily acid which separates is taken up in ether, washed with water, and dried over sodium sulfate. The ether is evaporated to leave the oily crude product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04150235uspto-grants-1979_04