Hexamethylenetetramine → HCID 15892664, compound

HRID 1900136Notes

Reaction equation

HRID 1900136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:27](O)=[O:28]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[CH:27]=[O:28]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 2757675HCID 2757675, compound

Product 1

HCID 15892664HCID 15892664, compound

Procedure

A mixture of 4.76 g of 3-chloro-4'-methylbiphenyl, 2.94 g of hexamethylenetetramine and 30 ml of trifluoroacetic acid is heated to boiling under reflux for 5 days. The reaction mixture is then concentrated and treated with ice-water, whereupon it is stirred for 15 minutes, made basic with sodium carbonate and extracted with ether. After evaporation of the ethereal extracts and chromatography of the residue on silica gel with methylene chloride/methanol 9:1 as the eluent, there is obtained 2-chloro-4-(4'-methylphenyl)benzaldehyde, b.p. 210°-215°C./25 Pa.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 days
  3. concentrationThe reaction mixture is then concentrated
  4. additiontreated with ice-water, whereupon it
  5. extractionextracted with ether
  6. customAfter evaporation of the ethereal extracts and chromatography of the residue on silica gel with methylene chloride/methanol 9:1 as the eluent

Sources & evidence

ORD record
ord-24e2b7fbbcfe4bceb232a556e19eb6e9
Source dataset
uspto-grants-1996_11
Patent number
US05574071

Reaction notes

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