4-Phenoxyphenol → 2-(4-Phenoxyphenoxy)cyclopentan-1-ol

HRID 46781

Reaction equation

HRID 46781 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].C([NH+]([CH2:21][CH3:22])CC)C>C(Cl)(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:22]2[CH2:21][CH2:4][CH2:3][CH:2]2[OH:1])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 132544-PhenoxyphenolHCID 3014304Triethylammonium iodide

Product 1

HCID 222476762-(4-Phenoxyphenoxy)cyclopentan-1-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 18.6 g of 4-phenoxyphenol, 12.8 g of 1,2-carbonyldioxycyclopentane and 4.6 g of triethylammonium iodide is stirred for 7 hours at 150° C. After cooling, the reaction mixture is taken up in chloroform. The solution is washed with water and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated by rotary evaporation. Fractional distillation of the residue yields (2-(4-phenoxyphenoxy)-cyclopentan-1-ol as a colourless oil with a melting point of 181°-185° C./0.001 torr.

Workup

  1. temperatureAfter cooling
  2. washThe solution is washed with water and once with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by rotary evaporation
  5. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-548d1b3741fe4d498d99cad709f385ba
Source dataset
uspto-grants-1979_11
Patent number
US04175137

Linked notes

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