Phenol → Salicylaldehyde

HRID 1824908Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:20](O)=[O:21]>>[CH:20]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])=[O:21]

Participants

Reactant 3

HCID 996Phenol

HCID 4101Hexamethylenetetramine

HCID 6422Trifluoroacetic acid

Product 1

HCID 6998Salicylaldehyde

Procedure

A mixture of an appropriate phenol and hexamethylenetetramine are treated with an appropriate acid, such as trifluoroacetic acid, to provide upon aqueous workup the corresponding o-formylphenol. This o-formylphenol is then treated with (bromomethyl)triphenylphosphonium bromide followed by an appropriate base such as potassium tert-butoxide to provide the desired benzofuran.

Sources & evidence

ORD record: ord-174dda12568748c19a3510d459c2ab31
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045545B1

Reaction notes

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