Formaldehyde → HCID 21568953, compound

HRID 1579633Notes

Reaction equation

HRID 1579633 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[O:10][C:6]=2[CH:5]=[C:4]([C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])[C:3]=1[CH3:20].C=O.Cl.[CH3:24]NC>O1CCOCC1>[CH3:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[O:10][C:6]=2[CH:5]=[C:4]([C:14](=[O:19])[C:15](=[CH2:24])[CH2:16][CH2:17][CH3:18])[C:3]=1[CH3:20]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21568964HCID 21568964, compound

Product 1

HCID 21568953HCID 21568953, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4,5-dimethyl-6-valerylbenzofuran-2-carboxylic acid (15 g.) paraformaldehyde (3.5 g.) and dimethylamine hydrochloride (7 g.) in p-dioxane (100 ml.) is refluxed for 8 hours and cooled. The 4,5-dimethyl-6-[(2-dimethylaminomethyl)valeryl]benzofuran-2-carboxylic acid hydrochloride which separates is filtered, dried, and dissolved in acetic acid (200 ml.) containing sodium acetate (20 g.). The reaction mixture is refluxed for two hours then poured into water (250 ml.) containing hydrochloric acid (25 ml.) affording 4,5 -dimethyl-6-(2-methylenevaleryl)-benzofuran-2-carboxylic acid which melts at 172° after recrystallization from butyl chloride.

Workup

  1. temperatureis refluxed for 8 hours
  2. temperaturecooled
  3. filtrationThe 4,5-dimethyl-6-[(2-dimethylaminomethyl)valeryl]benzofuran-2-carboxylic acid hydrochloride which separates is filtered
  4. customdried
  5. dissolutiondissolved in acetic acid (200 ml.)
  6. additioncontaining sodium acetate (20 g.)
  7. temperatureThe reaction mixture is refluxed for two hours
  8. additionthen poured into water (250 ml.)
  9. additioncontaining hydrochloric acid (25 ml.)

Sources & evidence

ORD record
ord-21ae8b892356496db0fb04d0a7b71d10
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

Loading…