Water → HCID 69133737, compound

HRID 457489Notes

Reaction equation

HRID 457489 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-c8ee324e43a84d999fc4ccd4361880c4
Source dataset
uspto-grants-2007_03
Patent number
US07189702B2

Reaction notes

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