Vanillin → 4,4'-[[1-(Hydroxymethyl)-1,2-ethanediyl]bis(oxy)]bis[3-methoxybenzaldehyde]

HRID 579823Notes

Reaction equation

[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Br[CH:13]([CH2:16]Br)[CH2:14][OH:15]>>[OH:15][CH2:14][CH:13]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])[CH2:16][O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

Reactant 2

HCID 1183Vanillin

HCID 72812,3-Dibromo-1-propanol

Product 1

HCID 201365834,4'-[[1-(Hydroxymethyl)-1,2-ethanediyl]bis(oxy)]bis[3-methoxybenzaldehyde]Yield 71.8%

Procedure

Vanillin (30.4 g, 0.2 m) is reacted with 2,3-dibromopropanol (21.8 g, 0.1 mol) according to the procedure employed in Example 41 to obtain 25.86 g of 4,4'-[[1-(hydroxymethyl)-1,2-ethanediyl]bis(oxy)]bis[3-methoxybenzaldehyde]. This intermediate (3.60 g, 0.01 m) is reacted with ethyl cyanoacetate as described in Example 41 to yield 4.3 g of product which mas spectroscopy indicated had the structure: ##STR32## When dissolved in methylene chloride, the product has an absorption maximum (λmax) at 361 nm.

Sources & evidence

ORD record: ord-684b784c5a044e139ca6c4125f7cba2d
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749774

Reaction notes

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