Benzene → m-(2,2-Dimethoxyethoxy)benzaldehyde

HRID 1577285Notes

Reaction equation

HRID 1577285 reaction equation
[OH-:1].[Na+].[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6]Br.[CH:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16]([O:18]CCO)C>>[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][O:1][C:10]1[CH:15]=[C:14]([CH:13]=[CH:12][CH:11]=1)[CH:16]=[O:18]

Participants

5

Reactant 4

HCID 241BenzeneHCID 8076Glycol monoethyl etherHCID 14798Sodium HydroxideHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 20572041m-(2,2-Dimethoxyethoxy)benzaldehyde

Procedure

In 20 ml of 2-ethoxyethyl alcohol, 1.65 g of sodium hydroxide and 4.88 g of m-hydroxybenzaldehyde were dissolved by heating. The resultant solution and 7.4 g of bromoacetaldehyde dimethyl acetal were refluxed for 22 hours. Then, the reaction solution was combined with 50 ml of benzene, washed with water, and further washed with an aqueous sodium hydroxide solution until total disappearance of the unaltered portion of hydroxybenzaldehyde and thereafter dried with anhydrous potassium carbonate. By distilling the resultant aqueous solution, there was obtained 3.6 g of m-(2,2-dimethoxyethoxy)benzaldehyde with a boiling point of 138° C./3 mmHg.

Workup

  1. temperatureby heating
  2. washwashed with water
  3. washfurther washed with an aqueous sodium hydroxide solution until total disappearance of the unaltered portion of hydroxybenzaldehyde
  4. dry with materialdried with anhydrous potassium carbonate
  5. distillationBy distilling the resultant aqueous solution

Sources & evidence

ORD record
ord-fb28e2c4148841d9bcefd8ae7e92f12e
Source dataset
uspto-grants-1981_09
Patent number
US04287335

Reaction notes

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