Ammonium Chloride → 6-Ethoxy-6-methylheptan-2-ol

HRID 1414828Notes

Reaction equation

HRID 1414828 reaction equation
[CH2:1]([O:3][C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][CH2:7][C:8](=[O:10])[CH3:9])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(OCC)C>[CH2:1]([O:3][C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][CH2:7][CH:8]([OH:10])[CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 214852226-Ethoxy-6-methylheptan-2-one

Product 1

HCID 227498296-Ethoxy-6-methylheptan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 43 g. of 6-ethoxy-6-methyl-2-heptanone in 100 ml. of absolute diethyl ether is slowly added dropwise with ice cooling to a suspension of 4.5 g. of lithium aluminum hydride in 400 ml. of absolute diethyl ether. The mixture is subsequently stirred for a further one hour at ca. 5° C. and then hydrolyzed by the cautious addition of a dilute aqueous ammonium chloride solution. The mixture is filtered through diatomaceous earth and the organic phase washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated under reduced pressure. By distillation there is obtained pure 6-ethoxy-6-methyl-2-heptanol of boiling point 100° C./10 mmHg; nD20 = 1.4372.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. washthe organic phase washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. distillationBy distillation there

Sources & evidence

ORD record
ord-316c6cd9a3354cd5b81671d15fed8046
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

Loading…