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

HRID 1707519Notes

Reaction equation

HRID 1707519 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([CH:12]([C:18](OCC)=[O:19])[C:13](OCC)=[O:14])[CH2:8][CH2:9][CH2:10][CH3:11].Cl>C1COCC1>[CH2:7]([CH:12]([CH2:18][OH:19])[CH2:13][OH:14])[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80167Diethyl pentylmalonateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 1175092-Pentyl-1,3-propanediolYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

34 g (0.9 mol) of LiAlH4 was dispersed in 690 cm3 of anhydrous THF, and 159 g (0.69 mol) of diethyl pentylmalonate was added dropwise under stirring. After the dropping was completed, it was refluxed for 2 hours in a hot water bath, and after cooling to room temperature, the excess LiAlH4 was decomposed by dropwise addition of THF including 10% water. 500 cm3 of concentrated hydrochloric acid was added, it was extracted with chloroform and washed in 10% HC1 and water. The chloroform was removed, and the remaining oily substance was distilled under reduced pressure (b. p. 110° C./4 mmHg) to obtain 76 g (0.52 mol) of 2-pentylpropane-1,3diol).

Workup

  1. temperatureit was refluxed for 2 hours in a hot water bath
  2. extractionit was extracted with chloroform
  3. washwashed in 10% HC1 and water
  4. customThe chloroform was removed
  5. distillationthe remaining oily substance was distilled under reduced pressure (b. p. 110° C./4 mmHg)

Sources & evidence

ORD record
ord-15890c0707014363b6b824269830304c
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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