4(2-Chloroallyl)benzaldehyde → 4(2-Chloroallyl)benzyl alcohol

HRID 1761788Notes

Reaction equation

HRID 1761788 reaction equation
[Cl:1][C:2](=[CH2:12])[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Cl:1][C:2](=[CH2:12])[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 132432814(2-Chloroallyl)benzaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 132432854(2-Chloroallyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The aldehyde (0.25 g) of Example 1 in ether (5 ml) is added to lithium aluminum hydride (0.03 g) in ether (5 ml), and the mixture stirred at 20° for 1 hour. After successive dropwise additions of water (30 μl), 15% NaOH (30 μl) and water (90 μl), the resulting clear ether layer (+ washings) is evaporated to a residue of 4(2-chloroallyl)benzyl alcohol yield 0.22 g (86%) nD20 1.5504.

Workup

  1. customAfter successive dropwise additions of water (30 μl), 15% NaOH (30 μl) and water (90 μl), the resulting clear ether layer (+ washings) is evaporated to a residue of 4(2-chloroallyl)benzyl alcohol yield 0.22 g (86%) nD20 1.5504

Sources & evidence

ORD record
ord-18d434c1f7874399a1be9583a9a099e5
Source dataset
uspto-grants-1989_05
Patent number
US04827051

Reaction notes

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