Acetone → 1,3-Propanediol, 2-(4-pentenyl)-

HRID 247696

Reaction equation

HRID 247696 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:12]([C:18](OCC)=[O:19])[C:13](OCC)=[O:14])[CH2:8][CH2:9][CH:10]=[CH2:11].CC(C)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:7]([CH:12]([CH2:18][OH:19])[CH2:13][OH:14])[CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 361718Diethyl 2-pent-4-enylpropanedioateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 110947511,3-Propanediol, 2-(4-pentenyl)-Yield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 13.8 g of lithium aluminium hydride in 500 ml of tetrahydrofuran was treated dropwise under nitrogen at 0°-5° C. within 1 hour with a solution of 33.2 g of diethyl (4-pentenyl)malonate in 125 ml of tetrahydrofuran. The mixture was stirred overnight at room temperature and then heated to boiling for 3 hours. After cooling there were cautiously added dropwise to the reaction mixture firstly 25 ml of acetone and then 25 ml of saturated sodium hydrogen carbonate solution. The resulting slurry was suction filtered and the residue on the suction filter was washed four times with tetrahydrofuran. Concentration of the filtrate gave 17.8 g of 2-(4-pentenyl)-1,3-propanediol (purity 89%) as a yellow liquid.

Workup

  1. temperatureheated
  2. waitto boiling for 3 hours
  3. temperatureAfter cooling there
  4. filtrationfiltered
  5. filtrationthe residue on the suction filter
  6. washwas washed four times with tetrahydrofuran

Sources & evidence

ORD record
ord-2cfe4bbc3277479d8c5031fa66304d2a
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Linked notes

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