Hydrochloric Acid → HCID 13746839, compound

HRID 1731782Notes

Reaction equation

HRID 1731782 reaction equation
C[O:2][C:3]1[C:8]([C:9]#[N:10])=[C:7]([O:11]C)[C:6]([O:13]C)=[C:5]([O:15]C)[C:4]=1[O:17]C.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[OH:2][C:3]1[C:8]([C:9]#[N:10])=[C:7]([OH:11])[C:6]([OH:13])=[C:5]([OH:15])[C:4]=1[OH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 19799329HCID 19799329, compound

Product 1

HCID 13746839HCID 13746839, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Four and three-tenths grams of pentamethoxybenzonitrile were refluxed in 12.5 g. of anhydrous aluminum chloride and 125 ml. of toluene for three hours after which time the suspension was poured into a mixture of 50 ml. of 12N aqueous hydrochloric acid and 200 g. of ice. The toluene layer was separated and the product recovered from the aqueous layer by filtration. Recrystallization from an ethyl acetate/toluene solvent mixture yielded pentahydroxybenzonitrile decomposing at 238° C. with a prior slight decomposition at 220° C.; yield =66%.

Workup

  1. customThe toluene layer was separated
  2. filtrationthe product recovered from the aqueous layer by filtration
  3. customRecrystallization from an ethyl acetate/toluene solvent mixture

Sources & evidence

ORD record
ord-f3268c46567f42b2a313d1a642b9f5c0
Source dataset
uspto-grants-1986_11
Patent number
US04623659

Reaction notes

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