Hydrochloric Acid → 2-Hydroxy-4,5-dimethoxybenzaldehyde

HRID 2364917Notes

Reaction equation

HRID 2364917 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1N2CN3CN(C2)CN1C3.Cl.FC(F)(F)[C:25](O)=[O:26]>>[OH:11][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][C:6]=1[CH:25]=[O:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 162513,4-Dimethoxyphenol

Product 1

HCID 109869082-Hydroxy-4,5-dimethoxybenzaldehyde

Procedure

In a 500 mL recovery flask, 5.0 g (32.4 mmol) of 3,4-dimethoxyphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 18.2 g (130 mmol, 4.0 eq) of hexamethylenetetramine (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 100 ml of trifluoroacetic acid (manufactured by Kanto Chemical Co., Inc.) and reacted at 100° C. for 24 hours. After the reaction was completed, in an ice bath, 200 ml of 1 N hydrochloric acid was added thereto and the resultant was stirred for 15 minutes. After the stirring was completed, the resultant was extracted with chloroform to obtain an extract. The extract was washed with hydrochloric acid and saturated saline, thereby obtaining 2.17 g (11.0 mmol) of 2-hydroxy-4,5-dimethoxybenzaldehyde.

Workup

  1. customreacted at 100° C. for 24 hours
  2. customAfter the reaction was completed, in an ice bath
  3. extractionthe resultant was extracted with chloroform
  4. customto obtain an extract
  5. washThe extract was washed with hydrochloric acid and saturated saline

Sources & evidence

ORD record
ord-c329b91a9b4e43ae92150c3e8d5327c6
Source dataset
uspto-grants-2014_04
Patent number
US08697332B2

Reaction notes

Loading…