Benzaldehyde → Benzal chloride

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:9].[Cl-:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH:1]([Cl:10])([Cl:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 240Benzaldehyde

HCID 13797396Triphenylphosphane dichloride

Product 1

HCID 7411Benzal chlorideYield 45%

Procedure

Furthermore, it is known from Liebig's Annalen der Chemie, Volume 626, pages 26 to 34 (1959) to react benzaldehyde with triphenylphosphine dichloride to give benzal chloride, but the yield is only 59%. When cyclohexanone is reacted with triphenylphosphine dichloride in the presence of an equimolar amount of triethylamine it is not the corresponding geminal dihalide which is obtained but 1-chlorocyclohex-1-ene in 45% yield (loc. cit., page 33).

Sources & evidence

ORD record: ord-72beb27f2df144ba840b75f81578cf24
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04044060

Reaction notes

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