HCID 21568262, compound → Ethyl 2,6-diethoxy-4-formylbenzoate

HRID 1579313Notes

Reaction equation

HRID 1579313 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:8]([C:14](Cl)=[O:15])=[CH:7][C:6]=1[O:17][CH2:18][CH3:19])[CH3:2].[S].N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd]>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:8]([CH:14]=[O:15])=[CH:7][C:6]=1[O:17][CH2:18][CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 21568262HCID 21568262, compoundHCID 178418361HCID 178418361, compoundHCID 178527711HCID 178527711, compound

Product 1

HCID 20288848Ethyl 2,6-diethoxy-4-formylbenzoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 12 g. of 4-(chloroformyl)-2,6-diethoxy-benzoic ethyl ester, 1.4 g. of palladium/barium sulfate catalyst (5%) and 0.2 ml. of quinoline sulfur regulator are heated under an atmosphere of nitrogen at 120° with stirring. Thereafter, hydrogen is passed through the reaction mixture at 120° until 90% of the theoretical amount of acid salt is freed. The reduction is stopped, and the suspension under an atmosphere of nitrogen is cooled to 25°. The catalyst is removed by filtration and the filtrate is evaporated to dryness under vacuum, whereby there is obtained 2,6-diethoxy-4-formylbenzoic acid ethyl ester as a colorless oil. A sample after recrystallization from low boiling petroleum ether yields pure 2,6-diethoxy-4-formylbenzoic acid ethyl ester having a m.p. of 45°-46°.

Workup

  1. additionA mixture of 12 g
  2. customis passed through the reaction mixture at 120° until 90% of the theoretical amount of acid salt
  3. temperaturethe suspension under an atmosphere of nitrogen is cooled to 25°
  4. customThe catalyst is removed by filtration
  5. customthe filtrate is evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-4d1c11da974d4b5db6e4f9d41df0df1f
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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