1-Octanol → HCID 86594669, compound

HRID 1454743Notes

Reaction equation

HRID 1454743 reaction equation
[Na].[CH2:2]([OH:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Cl[CH2:12][CH:13]([OH:16])[CH2:14][OH:15]>C(OCC)C>[CH2:2]([O:10][CH2:12][CH:13]([CH2:14][OH:15])[OH:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:12][CH2:13][O:10][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 72903-Chloro-1,2-propanediolHCID 5360545Sodium

Product 1

HCID 86594669HCID 86594669, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
105 °C

Procedure

23 g (1 mol) of sodium were added in portions over the course of 4 hours to 325 g (2.5 mol) of 1-octanol while stirring at 105° C. (the temperature did not rise above 120° C. during this). The mixture was stirred at 115° C. for 1 hour. Subsequently, 110.5 g (1 mol) of 3-chloro-propane-1,2-diol were added over the course of 2 hours, and the mixture was stirred at 120° C. for 3 hours. After cooling, the mixture was taken up in 400 ml of diethyl ether and extracted 3× with a total of 700 ml of water. The ethereal phase was dried over sodium sulphate and concentrated. The residue was distilled in vacuo.

Workup

  1. customdid not rise above 120° C.
  2. stirringThe mixture was stirred at 115° C. for 1 hour
  3. stirringthe mixture was stirred at 120° C. for 3 hours
  4. temperatureAfter cooling
  5. extractionextracted 3× with a total of 700 ml of water
  6. dry with materialThe ethereal phase was dried over sodium sulphate
  7. concentrationconcentrated
  8. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-b8b3502450b54c19bc3847a68e635c3e
Source dataset
uspto-grants-2009_01
Patent number
US07481973B2

Reaction notes

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