Vanillin → HCID 54205624, compound

HRID 2058742Notes

Reaction equation

CO[C:3]1[CH:8]=[C:7]([C:9]([CH3:14])=[CH:10][N+:11]([O-:13])=[O:12])[CH:6]=[CH:5][C:4]=1O.[O:16]=CC1C=CC(O)=C(OC)C=1.[N+](CC)([O-])=O>>[CH3:14][C:9]([C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][C:8]=1[OH:16])=[CH:10][N+:11]([O-:13])=[O:12]

Participants

Reactant 3

HCID 1183Vanillin

HCID 6587Nitroethane

HCID 54218829HCID 54218829, compound

Product 1

HCID 54205624HCID 54205624, compoundYield 80%

Procedure

2-methoxy-4-(α-methyl-β-nitroethenyl)-phenol was also prepared by a variation of the above procedure in which vanillin was treated with nitroethane instead of nitromethane. The conditions employed for the reaction, however, were essentially the same as those described above for nitromethylation. The α-methyl-β-nitroethenyl phenol product was obtained in 80% yield with m.p. 110°-112° and had λ max (ethanol) of 368 and λ max (TRIS 8.8) of 475 with ε of 13,100.

Workup

customThe conditions employed for the reaction

Sources & evidence

ORD record: ord-21b8cac9c7724a4eb8c9add7733416b4
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04318986

Reaction notes

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