3-Methylbenzaldehyde → HCID 12813780, compound

HRID 1733288Notes

Reaction equation

HRID 1733288 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].O[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>[OH-].[Na+]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]1[CH2:11][C:12](=[O:13])[C:14]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:6]1

Participants

4

Reactant 2

HCID 121053-MethylbenzaldehydeHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 12813780HCID 12813780, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3-methylbenzaldehyde (12 g, 0.1 mol), 2-hydroxyacetophenone (13.6 g, 0.1 mol), and 2 liters of 0.1 N NaOH was stirred at room temperature for 4 days. The reaction was extracted with ether and the ether dried and evaporated to give 20.5 g of 3'-methyl flavanone as an oil. The oil, not further purified but used directly, was converted in a similar manner as described in Example 1 into 8.2 g of the hydrochloride salt of 3'-methyl-3-dimethylaminomethyl flavanone, as a solid, m.p. 156°-158° C.

Workup

  1. extractionThe reaction was extracted with ether
  2. dry with materialthe ether dried
  3. customevaporated

Sources & evidence

ORD record
ord-7aee0642a74546ee8ce115a441170e72
Source dataset
uspto-grants-1980_12
Patent number
US04241069

Reaction notes

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