Ethylene carbonate → HCID 13753176, compound

HRID 1732156Notes

Reaction equation

HRID 1732156 reaction equation
[C:1]1(=O)[O:5][CH2:4][CH2:3][O:2]1.[F:7][C:8]1[CH:21]=[CH:20][C:11]([O:12][C:13]2[CH:18]=[CH:17]C(O)=[CH:15][CH:14]=2)=[CH:10][CH:9]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:7][C:8]1[CH:21]=[CH:20][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:1]([O:5][CH2:4][CH2:3][OH:2])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 7303Ethylene carbonate2×HCID 129406244-(4-Fluorophenoxy)phenol

Product 1

HCID 13753176HCID 13753176, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

6.8 g of ethylene carbonate and 2.3 g of tetrabutylammonium bromide are added to a solution of 13.8 g of p-(p-fluorophenoxy)phenol in 35 ml of dimethylformamide. After 4 hours at reflux there are added an additional 1.2 g of ethylene carbonate, and the mixture is heated at reflux for an additional 2 hours. The cooled mixture is poured into 150 ml of ice/water and extracted three times with 100 ml of ethyl acetate each time. The extracts are washed twice with 100 ml of saturated sodium chloride solution each time, dried and evaporated. The residue is purified by recrystallization from n-hexane/ethyl acetate to yield pure 2-[p-(p-fluorophenoxy)-phenoxy]-ethanol, m.p. 74°-76° C.

Workup

  1. temperatureAfter 4 hours at reflux there
  2. temperaturethe mixture is heated
  3. temperatureat reflux for an additional 2 hours
  4. extractionextracted three times with 100 ml of ethyl acetate each time
  5. washThe extracts are washed twice with 100 ml of saturated sodium chloride solution each time
  6. customdried
  7. customevaporated
  8. customThe residue is purified by recrystallization from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-3e2b13758cf642e1984788f8d8ff370c
Source dataset
uspto-grants-1986_11
Patent number
US04625048

Reaction notes

Loading…