4-Hydroxybenzaldehyde → HCID 54521202, compound

HRID 2073529Notes

Reaction equation

HRID 2073529 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N:10]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:11]=1[CH3:12].[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:12][C:11]2[CH:13]=[CH:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)=[CH:4][CH:3]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 70602-MethylquinolineHCID 7918Acetic Anhydride

Product 1

HCID 54521202HCID 54521202, compound

Conditions

Temperature
130 °C

Procedure

A solution of 25 g of p-hydroxybenzaldehyde and 28 ml of quinaldine is 100 ml of acetic anhydride are heated at 130° C. overnight. The reaction mixture is concentrated in vacuo and then passed through a flash silica gel column slurry packed with hexanes and eluted with 15% acetone in hexanes. Concentration of the desired fractions gives a yellow solid which is recrystalized from Et2O/hexanes to give 2-(2-(4-acetoxyphenyl)ethenyl)quinoline (M.P. 127°-128° C.).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washeluted with 15% acetone in hexanes
  3. customConcentration of the desired fractions gives a yellow solid which
  4. customis recrystalized from Et2O/hexanes

Sources & evidence

ORD record
ord-de4358bba6ae4a4f94486cbc632c323f
Source dataset
uspto-grants-1990_04
Patent number
US04918081

Reaction notes

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