4-Hydroxybenzaldehyde → HCID 682482, compound

HRID 326172Notes

Reaction equation

HRID 326172 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 79634-Methylpyridine

Product 1

HCID 682482HCID 682482, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

By the reaction of 20.0 g of γ-picolin and 26.2 g of p-hydroxybenzaldehyde in 65.8 g of acetic anhydride, there was obtained 4-[2-(4-hydroxyphenyl)-ethenyl]-pyridine. In 10 cm3 of N,N-dimethylacetamide, 2 g of the reaction product was dissolved and 1.23 g of triethylamine was further added thereto. This mixture was ice cooled and 1.34 g of methacrylic acid chloride was dropwise added thereto. After the reaction was completed, water was added to deposit crystals, which were separated by filtration. The separated crystals were recrystallized via a mixed solvent of ethyl acetate and hexane, to afford 2.16 g (80% in yield) of 4-[2-(4-methacryloyloxyphenyl)-ethenyl]-pyridine. The melting point of the crystals was 156° to 158° C.

Sources & evidence

ORD record
ord-4fabe4c8ef6b46daa4df3c6430afbb59
Source dataset
uspto-grants-1984_04
Patent number
US04444868

Reaction notes

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