Hydrochloric Acid → 1-Propanol, 2-(octyloxy)-

HRID 1885108Notes

Reaction equation

HRID 1885108 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:15][CH:16]([CH3:22])[C:17](OCC)=[O:18])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl>C(OCC)C>[CH2:7]([O:15][CH:16]([CH3:22])[CH2:17][OH:18])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14692867HCID 14692867, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 100582981-Propanol, 2-(octyloxy)-Yield 86.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Then, 7.5 g of LiAlH4 was added to 250 ml of diethyl ether, followed by stirring for a little while. Then, a solution of 56 g of the above ester in 50 ml of diethyl ether was added dropwise in 2 hours at below 5° C. After the addition, the mixture was stirred at room temperature for 2 hours and allowed to stand for 15 hours. After the reaction, 30 ml of 5% hydrochloric acid was added, and 6N-hydrochloric acid was added to provide a pH of about 1, followed by extraction with ether. The product was washed with water, dried and subjected to removal of the solvent by distillation, followed by vacuum distillation to obtain 39.5 g of 2-octyloxypropanol as a fraction of 107° C./3 mmHg.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. additionwas added
  4. customto provide a pH of about 1
  5. extractionfollowed by extraction with ether
  6. washThe product was washed with water
  7. customdried
  8. customsubjected to removal of the solvent by distillation
  9. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-25c19f88f67b4793b62715c58c1810b4
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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