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

HRID 46780

Reaction equation

HRID 46780 reaction equation
[O:1]([C:8]1[CH:19]=[CH:18][C:11]([O:12][C:13]2[CH:14]=[CH:15][CH2:16][CH:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:20].[BH4-].[Na+]>O1CCCC1.[OH-].[Na+].C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH:14]2[OH:20])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 203857513-(4-Phenoxyphenoxy)-cyclopenten-1-ene

Product 1

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

Reagents, catalysts & solvents 3

HCID 15337Mercuric acetateCatalystHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent2×

Procedure

A solution of 12.6 g of 3-(4-phenoxyphenoxy)-cyclopenten-1-ene in 25 ml of tetrahydrofurane is added dropwise in the course of 1 hour to a mixture of 15.9 g of mercury(II) acetate, 35 ml of water and 50 ml of tetrahydrofurane. The mixture is stirred for about 15 hours at room temperature, then 50 ml of 3 N sodium hydroxide solution are added dropwise in the course of 11/2 hours, followed by the dropwise addition in the course of 1 hour of 50 ml of a 0.5 N solution of sodium borohydride in 3 N sodium hydroxide solution. The reaction mixture is stirred for 2 hours at room temperature and precipitated mercury is removed by filtration. The filtrate is poured into ice-water and, after extraction with ether, the organic phase is washed 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. stirringThe reaction mixture is stirred for 2 hours at room temperature
  2. customprecipitated mercury
  3. customis removed by filtration
  4. additionThe filtrate is poured into ice-water
  5. extractionafter extraction with ether
  6. washthe organic phase is washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by rotary evaporation
  9. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-68dcc8e1681f4418be9cbbb7c7b244ab
Source dataset
uspto-grants-1979_11
Patent number
US04175137

Linked notes

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