2-Chloroveratraldehyde → 4-Chloro-1,3-benzodioxole-5-methanol

HRID 427284Notes

Reaction equation

HRID 427284 reaction equation
[Cl:1][C:2]1[C:9]([O:10]C)=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].ClC1C2OCOC=2C=CC=1C=O.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:9]2[O:10][CH2:13][O:12][C:8]=2[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 794452-ChloroveratraldehydeHCID 4311764Sodium borohydrideHCID 217955384-Chloro-1,3-benzodioxole-5-carboxaldehyde

Product 1

HCID 217955394-Chloro-1,3-benzodioxole-5-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-3,4-dimethoxybenzaldehyde was converted to 4-chloro-1,3-benzodioxole-5-carboxaldehyde by the method of S. T. Ross, R. G. Franz, J. W. Wilson, R. A. Hahn and H. M. Sarau, J. Heterocyclic Chemistry, (1986) 23, 1805. Reduction of the aldehyde was then carried out with sodium borohydride (1 equivalent) in THF at 0° C. to provide 4-chloro-1,3-benzodioxole-5-methanol (Examples 30A, 31 A).

Sources & evidence

ORD record
ord-f60acb3c539c43beb89640a4deff0810
Source dataset
uspto-grants-2001_11
Patent number
US06313100B1

Reaction notes

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