Hydrochloric Acid → HCID 54028115, compound

HRID 1885109Notes

Reaction equation

HRID 1885109 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:15][CH:16]([CH3:22])[CH2:17][CH2:18][C:19](O)=[O:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl>CCOCC>[CH2:7]([O:15][C@@H:16]([CH3:22])[CH2:17][CH2:18][CH2:19][OH:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19880012HCID 19880012, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54028115HCID 54028115, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
23 °C

Procedure

Into 210 ml of dry ether, 10 g of LiAlH4 was added, and under stirring, a solution of the above carboxylic acid in 70 ml of ether was added dropwise in 70 min. while keeping a temperature of 2°-6° C. after the addition, the mixture was raised in temperature to 23° C. and stirred for 3 hours. After standing for 12 hours, 5% hydrochloric acid was added to acidify the mixture while keeping a temperature of below 15° C., and the product was extracted with ether and washed successively with water, 5% NaOH aqueous solution and water, followed by drying with anhydrous MgSO4. By distilling off the solvent and effecting vacuum distillation, 10 g of (S)-4-octyloxypentanol was obtained as a fraction at 150° C./5 mmHg. The product showed the following IR data.

Workup

  1. customa temperature of 2°-6° C.
  2. additionafter the addition
  3. stirringstirred for 3 hours
  4. customa temperature of below 15° C.
  5. extractionthe product was extracted with ether
  6. washwashed successively with water, 5% NaOH aqueous solution and water
  7. dry with materialby drying with anhydrous MgSO4
  8. distillationBy distilling off
  9. distillationthe solvent and effecting vacuum distillation

Sources & evidence

ORD record
ord-316d3b2254304e86ac04238749905f91
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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