4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

HRID 1190766Notes

Reaction equation

HRID 1190766 reaction equation
C(=O)C1C=CC=CC=1.OC1C=CC(C=O)=CC=1.BrCCBr.[Br:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[O:36][CH2:35][CH2:34][O:33]2)=[CH:28][CH:27]=1.C1(=O)[NH:41]C(=O)C2=CC=CC=C12.[K]>CC(C)=O.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)CO>[Br:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][CH:27]=1.[O:33]1[CH2:34][CH2:35][O:36][CH:32]1[C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][NH2:41])=[CH:27][CH:28]=1

Participants

11

Reactant 5

HCID 1264-HydroxybenzaldehydeHCID 240BenzaldehydeHCID 78391,2-DibromoethaneHCID 13814327HCID 13814327, compoundHCID 24194345Phthalimide potassium salt

Product 2

HCID 2627064-(2-Bromoethoxy)BenzaldehydeHCID 69113361HCID 69113361, compound

Reagents, catalysts & solvents 4

HCID 6101p-Toluenesulfonic acidCatalystHCID 174Ethylene GlycolSolventHCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

In order to prepare a benzaldehyde conjugated alginate, a few appropriate precursors are first synthesized. 4-(2-bromoethoxy)benzaldehyde is prepared by reacting p-hydroxibezaldehyde with 1,2-dibromoethane, in dry acetone. The product is then reacted with ethyleneglycol in toluene, with para toluene sulfonic acid as a catalyst, in dry conditions, in order to afford protection to the labile aldehyde groups. The protected 2-(4-(2-bromoethoxy)phenyl)-1,3-dioxolane is then reacted with potassium phthalimide, to afford 2-(4-(1,3-dioxolan-2-yl)phenoxy)ethanamine which is next coupled to the alginate using carbodiimide chemistry (using EDAC and NHSS as activators for alginate), as described previously. Then, the protecting group on the 1,3-dioxolane is removed by PPTS, in ethanol, and the free aldehyde is obtained. Any ligand protein may now be coupled by creating a Schiff base bond between the activated alginate and the amino group of the protein.

Workup

  1. customto afford protection to the labile aldehyde groups

Sources & evidence

ORD record
ord-a57a7547d1844d0990989c654ad4038c
Source dataset
uspto-grants-2014_03
Patent number
US08679484B2

Reaction notes

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