Sodium borohydride → 2-(4-Phenoxyphenoxy)cyclopentan-1-ol

HRID 46778Notes

Reaction equation

HRID 46778 reaction equation
[BH4-].[Na+].[O:3]([C:10]1[CH:22]=[CH:21][C:13]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.CO>[O:3]([C:10]1[CH:22]=[CH:21][C:13]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[OH:20])=[CH:12][CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 203857412-(4-Phenoxyphenoxy)-cyclopentan-1-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.78 g of sodium borohydride in 10 ml of water is added at room temperature to a solution of 8.04 g of 2-(4-phenoxyphenoxy)-cyclopentan-1-one in 60 ml of methanol. The reaction mixture is stirred for 15 hours at room temperature and then concentrated under reduced pressure. The residue is poured into ice-water and extracted with ether. The organic phase is washed twice 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 boiling point of 181°-185° C./0.001 torr.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is poured into ice-water
  3. extractionextracted with ether
  4. washThe organic phase is washed twice with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by rotary evaporation
  7. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-2ef5f5af53484609ab6d59ece6adafd5
Source dataset
uspto-grants-1979_11
Patent number
US04175137

Reaction notes

Loading…