2-Chloroethanol → 4-(2-hydroxyethoxy)-3-methoxybenzaldehyde

HRID 247468Notes

Reaction equation

HRID 247468 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.[OH-].[Na+].Cl[CH2:15][CH2:16][OH:17]>O>[OH:17][CH2:16][CH2:15][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

5

Reactant 3

HCID 342-ChloroethanolHCID 1183VanillinHCID 14798Sodium Hydroxide

Product 1

HCID 31527124-(2-hydroxyethoxy)-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Vanillin (15.2 g, 0.01 m), water (70 mL), and sodium hydroxide (5.0 g, 0.0125 m) are mixed and stirred for a few minutes until solution is completed. 2-Chloroethanol (9.7 g, 0.012 m) is added and the reaction mixture heated at reflux for 16 hours and then cooled. The solid product is collected by filtration, washed with water, dried, and finally recrystallized from toluene. The yield is 13.0 g (69.9% of the theoretical yield).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 16 hours
  3. temperaturecooled
  4. filtrationThe solid product is collected by filtration
  5. washwashed with water
  6. customdried
  7. customfinally recrystallized from toluene
  8. customThe yield is 13.0 g (69.9% of the theoretical yield)

Sources & evidence

ORD record
ord-17fecfb0abf44957a35b62f0cac01ca7
Source dataset
uspto-grants-1987_11
Patent number
US04707537

Reaction notes

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