2,4-Difluorobenzaldehyde → 2,4-Difluoro-1-methylbenzene

HRID 365973

Reaction equation

HRID 365973 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.FC1C=C(F)C=CC=1CO>[Ni]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH3:4]

Participants

4

Reactant 2

HCID 737702,4-DifluorobenzaldehydeHCID 918672,4-Difluorobenzyl alcohol

Product 1

HCID 679832,4-Difluoro-1-methylbenzeneYield 68.6%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

DE-A 2,333,849 discloses that 2,4-difluorobenzaldehyde can be converted into 2,4-difluorobenzyl alcohol in a yield of 68.6% by hydrogenation over Raney nickel. Disadvantages of this process are not only the large amount of catalyst (31 g per mol) and the large amount of a solvent (1100 ml per mole) but also the unsatisfactory yield of 68.6%. These factors result in an unsatisfactory space-time yield. The aldehyde used was obtained here from the difficult-to-obtain 2,4-difluorotoluene by side-chain chlorination and subsequent hydrolysis.

Workup

  1. customThese factors result in an unsatisfactory space-time
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Sources & evidence

ORD record
ord-7abb27e4324043f09f8c1963b7bffe45
Source dataset
uspto-grants-2000_10
Patent number
US06127581

Linked notes

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