Water → 2-(2-Methylallyl)propane-1,3-diol

HRID 709799Notes

Reaction equation

HRID 709799 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8](=[CH2:19])[CH2:9][CH:10]([C:15](OC)=[O:16])[C:11](OC)=[O:12].O.[OH-].[Na+]>C1COCC1>[CH3:19][C:8](=[CH2:7])[CH2:9][CH:10]([CH2:15][OH:16])[CH2:11][OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 565665Propanedioic acid, (2-methyl-2-propenyl)-, dimethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 152978952-(2-Methylallyl)propane-1,3-diolYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (9.20 g) in THF (250 mL) was slowly added a solution of dimethyl 2-(2-methylallyl)malonate (13.0 g) in THF (20 mL) at 0° C. The reaction mixture was heated under reflux for 2 hr. Water (60 mL) and 15% aqueous sodium hydroxide solution (72 mL) were added to the reaction mixture, and the mixture was filtered and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (4.80 g) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hr
  3. filtrationthe mixture was filtered
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-ef4e9048d53749ecb973502aa6664a65
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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