Water → HCID 69133737, compound

HRID 7362Notes

Reaction equation

HRID 7362 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:11]1[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][CH:12]=1)=[CH:8][CH2:9][CH3:10].O.[OH-].[Na+]>C(OCC)C>[CH:7](/[C:11]1[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:19][CH:20]=1)=[CH:8]\[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69135322Methyl 4-(but-1-en-1-yl)benzoate

Product 1

HCID 69133737HCID 69133737, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (1.2 g) in diethyl ether (100 mL) was added a solution of methyl 4-(but-1-en-1-yl)benzoate (2.5 g) in diethyl ether (20 mL) at 0° C., and the mixture was heated under reflux for 30 mixture. After the reaction mixture was cooled to 0° C., to the mixture were added water (1.2 mL), an aqueous sodium hydroxide solution (15%, 1.2 mL) and water (3.6 mL), and the mixture was stirred at room temperature for 5 minutes. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give (E)-4-(but-1-en-1-yl)benzyl alcohol (1.9 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 mixture
  3. customInsoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ca3864fed8fc4967bdbb8ce498ef21c7
Source dataset
uspto-grants-2006_08
Patent number
US07087579B2

Reaction notes

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