Reaction #833524

Reaction equation

6-acetoxycyclohexane

Sodium hydroxide

dimethyl formamide

ethyl 3-(4-hydroxyphenyl)propionate

Sodium hydroxide

→

(4-(6-hydroxyhexyloxy)phenyl)propionic acid

Solvents

water

toluene

water

ethanol

Conditions

Workup

1. 1
   workup.STIRRINGstirred at 80° C. for 7 hours
2. 2
   workup.ADDITIONwas further added
3. 3
   workup.STIRRINGstirred
4. 4
   OtherAfter separation
5. 5
   Washthe toluene layer was washed with 6N hydrochloric acid
6. 6
   Dryingan aqueous saturated solution of sodium carbonate and water successively and then dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off from the toluene layer
8. 8
   Otherto obtain 709 g of concentrates
9. 9
   workup.ADDITIONwere added
10. 10
    Temperatureheated
11. 11
    Temperaturerefluxed for 2 hours
12. 12
    ConcentrationThe reaction mixture was concentrated under a reduced pressure
13. 13
    Otheran evaporator
14. 14
    workup.ADDITIONthe resultant concentrates were poured into 6N hydrochloric acid
15. 15
    FiltrationThe obtained slurry was filtered
16. 16
    Otherto obtain solids
17. 17
    OtherThey were recrystallized from ethanol

Procedure

Sodium hydroxide (98 g) was added to a solution of dimethyl formamide (2,800 mL) of ethyl 3-(4-hydroxyphenyl)propionate (400 g) and stirred at 40° C. for 30 minutes. Formation of a salt could be observed visually. 6-acetoxycyclohexane (515 g) was added and stirred at 80° C. for 7 hours. The reaction mixture was poured into water (2,000 mL) and, toluene was further added and stirred. After separation, the toluene layer was washed with 6N hydrochloric acid, an aqueous saturated solution of sodium carbonate and water successively and then dried over anhydrous magnesium sulfate. The solvent was distilled off from the toluene layer to obtain 709 g of concentrates. Sodium hydroxide (185 g) was dissolved in water (400 mL) to which ethanol (600 mL) and 709 g of the concentrates were added and heated and refluxed for 2 hours. The reaction mixture was concentrated under a reduced pressure by using an evaporator and the resultant concentrates were poured into 6N hydrochloric acid. The obtained slurry was filtered to obtain solids. They were recrystallized from ethanol to obtain (4-(6-hydroxyhexyloxy)phenyl)propionic acid (281 g). Melting point: 109° C. to 112° C.

Source