4(Z-3-chloroallyl)benzaldehyde → 4(Z-3-chloroallyl)benzyl alcohol

HRID 231670Notes

Reaction equation

HRID 231670 reaction equation
[Cl:1]/[CH:2]=[CH:3]\[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Cl:1]/[CH:2]=[CH:3]\[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 132433384(Z-3-chloroallyl)benzaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 132433484(Z-3-chloroallyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The aldehyde (0.22 g) of Example 1 in ether (5 ml) is added to lithium aluminium hydride (0.08 g) in ether (5 ml), and the mixture stirred at 20° for 1 hour. After successive dropwise additions of water (80 l), 15% NaOH (80 l) and water (240 l), the resulting clear ether layer (+ washings) is evaporated to a residue of 4(Z-3-chloroallyl)benzyl alcohol yield 0.19 g (86%) nD20 1.5529.

Workup

  1. customAfter successive dropwise additions of water (80 l), 15% NaOH (80 l) and water (240 l), the resulting clear ether layer (+ washings) is evaporated to a residue of 4(Z-3-chloroallyl)benzyl alcohol yield 0.19 g (86%) nD20 1.5529

Sources & evidence

ORD record
ord-b06ab0339a0c49c98a49f6a1670d1458
Source dataset
uspto-grants-1989_07
Patent number
US04847438

Reaction notes

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