Hydrochloric Acid → 2,2-Diisobutyl-1,3-propanediol

HRID 132736Notes

Reaction equation

HRID 132736 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:11]([CH2:22][CH:23]([CH3:25])[CH3:24])([C:17](OCC)=[O:18])[C:12](OCC)=[O:13])[CH:8]([CH3:10])[CH3:9].Cl>C(OCC)C>[CH2:7]([C:11]([CH2:22][CH:23]([CH3:25])[CH3:24])([CH2:12][OH:13])[CH2:17][OH:18])[CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10423387HCID 10423387, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 39856252,2-Diisobutyl-1,3-propanediolYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 3 g (0.079 mol) LiAlH4 was added 100 ml ethyl ether, then added 15.5 g (0.057 mol) diethyl 2,2-diisobutylmalonate dropwise with intensely stirring. The reaction mixture was heated refluxing for 5 hours, then poured into 100 g ice that was acidified with dilute hydrochloric acid. The mixture was extracted with ethyl ether. After remove ethyl ether from the extract, 2,2-diisobutyl-1,3-propandiol as a white solid was recrystallized from hexane, and the yield was 78%. m.p. 75-77° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxing for 5 hours
  3. extractionThe mixture was extracted with ethyl ether
  4. customAfter remove ethyl ether from the extract, 2,2-diisobutyl-1,3-propandiol as a white solid
  5. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-d04d84f18c1f4ce7924275c149c99132
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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