Ethanol → HCID 19829491, compound

HRID 1493884Notes

Reaction equation

HRID 1493884 reaction equation
OC([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)CCCCC.[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl.[OH-].[K+].[CH2:22]([OH:24])[CH3:23]>O>[OH:24][CH:22]([CH:18]1[O:19][CH:17]1[CH2:15][O:14][C:10]1[CH:9]=[CH:8][CH:13]=[CH:12][CH:11]=1)[CH2:23][CH2:9][CH2:8][CH2:13][CH3:12]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 117900843-(1-Hydroxyhexyl)phenol

Product 1

HCID 19829491HCID 19829491, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.4 g. (0.1 mole) 3-(1-hydroxyhexyl)-phenol and 28.6 g. epichlorohydrin are dissolved in 25 ml. ethanol and heated to the boil. A solution of 6.6 g. potassium hydroxide in 3 ml. water and 25 ml. ethanol is then added dropwise thereto in the course of 15 minutes. The reaction mixture is boiled under reflux for 2 hours, the solvent is then distilled off and the residue is taken up in water. Extraction is carried out with ethyl acetate, the ethyl acetate phase is washed twice with aqueous sodium hydroxide solution and water, dried and evaporated to give 22.4 g. (89% of theory) of the title compound in the form of an oil.

Workup

  1. customin the course of 15 minutes
  2. temperatureunder reflux for 2 hours
  3. distillationthe solvent is then distilled off
  4. extractionExtraction
  5. washthe ethyl acetate phase is washed twice with aqueous sodium hydroxide solution and water
  6. customdried
  7. customevaporated
  8. customto give 22.4 g

Sources & evidence

ORD record
ord-ac2c1377d029427d99d7036aacca91b8
Source dataset
uspto-grants-1991_06
Patent number
US05025028

Reaction notes

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