Water → HCID 57170919, compound

HRID 1003126Notes

Reaction equation

HRID 1003126 reaction equation
[CH2:1]([O:8][CH:9]([OH:14])[CH2:10][CH2:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17](Br)[CH3:18].O>O1CCCC1>[CH2:17]([O:14][CH:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH3:13])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 21621925HCID 21621925, compound

Product 1

HCID 57170919HCID 57170919, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 194 g (1 mol) of pentanediol monobenzyl ether in 1 L of tetrahydrofuran (hereinafter referred to THF) was added to a solution of 48 g (2 mol) of sodium hydride in 100 ml of THF under cooling. Then, the mixture was heated under reflux for 2 hours and cooled to the room temperature before 140 g (1.3 mol) of ethyl bromide in 300 ml of THF was added dropwise. The mixture was heated under reflux for 6 hours. 500 ml of water was added and extraction was carried out with 500 ml of diethyl ether. After the organic layer was neutralized and washed with water and dried over anhydrous magnesium sulfate and concentrated. The oily residue was purified by distillation under the reduced pressure, to obtain 192 g of pentanediol benzyl ethyl ether. Boiling point; 110-117° C. (1 mmHg).

Workup

  1. temperatureunder cooling
  2. temperatureThen, the mixture was heated
  3. temperatureunder reflux for 2 hours
  4. additionwas added dropwise
  5. temperatureThe mixture was heated
  6. temperatureunder reflux for 6 hours
  7. extractionextraction
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. distillationThe oily residue was purified by distillation under the reduced pressure

Sources & evidence

ORD record
ord-f5d1a8e360494d59a95437bf5be3878e
Source dataset
uspto-grants-2000_04
Patent number
US06045720

Reaction notes

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