4-Hydroxybenzaldehyde → 4-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde

HRID 2094804Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][N:17]=1)[OH:15].O>CN(C)C=O>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([CH:14]([OH:15])[CH2:13][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[N:17][CH:18]=1)[CH3:23]

Participants

Conditions

Temperature: 85 °C

Procedure

Into a solution of 9.635 kg (72.99 mol) of 4-hydroxy benzaldehyde dissolved in 50 lit. dimethylformamide was added 5.675 kg (236.45 mol) of sodium hydride in 5 lit. dimethylformamide and stirred for 15 min. To this was added 15 Kg (65.22 mol) of 2-bromo-1-(5-ethyl pyridin-2-yl)-ethanol dissolved in 500 lit dimethylformamide and stirring was continued for 1 hr. at 25 to 30° C. Reaction mixture was heated at 80 to 90° C. for 14 hr., allowed to cool to 25° C. and excess of water was added into it. Product was extracted with diethyl ether. Organic layer was dried (magnesium sulfate) and concentrated to obtain crude product, which was purified in methyl tert-butyl ether as described in example 17 to obtain 12.195 Kg (69%) pure 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde. m.p. 83° C.

Workup

dissolutiondissolved in 500
stirringstirring
waitwas continued for 1 hr
customat 25 to 30° C
customReaction mixture
additionwas added into it
extractionProduct was extracted with diethyl ether
dry with materialOrganic layer was dried (magnesium sulfate)
concentrationconcentrated
customto obtain crude product, which
customwas purified in methyl tert-butyl ether

Sources & evidence

ORD record: ord-73e1553641644889ad66ca535d3a4205
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445685B2

Reaction notes

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