Hydroquinone → 3-(p-Tolyl)acrylaldehyde

HRID 982554Notes

Reaction equation

HRID 982554 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C1(C=CC(O)=CC=1)O>C(O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 785HydroquinoneHCID 5897153-(4-Methylphenyl)prop-2-yn-1-ol

Product 1

HCID 5829413-(p-Tolyl)acrylaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 250 g of 75% strength aqueous formic acid, 50 g of p-methylphenylethynylcarbinol and 0.5 g of hydroquinone is refluxed for 1 hour and then worked up as described in Example 1 to give 40 g (corresponding to 80% of theory) of p-methylcinnamaldehyde having a boiling point of 90°-95° C./0.1 mbar.

Workup

  1. temperatureis refluxed for 1 hour

Sources & evidence

ORD record
ord-a740dbf13ca54fe3b35ce19d13a20f02
Source dataset
uspto-grants-1991_02
Patent number
US04996365

Reaction notes

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