Phenol → 1-Hexanol, 6-phenoxy-

HRID 2051901Notes

Reaction equation

HRID 2051901 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Cl[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19]>CN(C)P(N(C)C)(N(C)C)=O.O>[O:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 748286-Chloro-1-hexanolHCID 178418361HCID 178418361, compound

Product 1

HCID 122932151-Hexanol, 6-phenoxy-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 10.3 g of phenol in 25 ml of hexamethylphosphoramide is added 4.2 g of 57% sodium hydride in oil. After hydrogen evolution ceases, 13.6 g of 6-chlorohexan-1-ol in 25 ml of hexamethylphosphoramide is added and the mixture heated at 110° C. for 16 hours. The solution is cooled, diluted with water and extracted with ether. The ether extracts are washed with sodium hydroxide solution, dried (magnesium sulfate) and the solvent removed under vacuum to give white crystals, mp 69°-74° C.

Workup

  1. temperatureThe solution is cooled
  2. extractionextracted with ether
  3. washThe ether extracts are washed with sodium hydroxide solution
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent removed under vacuum
  6. customto give white crystals, mp 69°-74° C.

Sources & evidence

ORD record
ord-059f2b2644d8433e8ef61f744a93edf6
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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