Water → 4-(Cyclopropylidenemethyl)benzyl alcohol

HRID 457484Notes

Reaction equation

HRID 457484 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(=[CH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][CH:12]=2)[CH2:9][CH2:8]1.O>O1CCCC1>[C:7]1(=[CH:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:19][CH:20]=2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 11600812Methyl 4-(cyclopropylidenemethyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 691337364-(Cyclopropylidenemethyl)benzyl alcoholYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (0.16 g) in tetrahydrofuran (30 mL) was added methyl 4-(cyclopropylidenemethyl)benzoate (0.80 g), and the mixture was stirred at room temperature for 5 hours. Water (0.4 mL) was added to the reaction mixture, and the mixture was stirred for 3 days. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give 4-(cyclopropylidenemethyl)benzyl alcohol (0.69 g).

Workup

  1. stirringthe mixture was stirred for 3 days
  2. customInsoluble materials were removed by filtration
  3. customthe solvent of the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-40c37aa83b424274badc6f032b09f87a
Source dataset
uspto-grants-2007_03
Patent number
US07189702B2

Reaction notes

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