Hydrochloric Acid → HCID 21568960, compound

HRID 1579624Notes

Reaction equation

HRID 1579624 reaction equation
[C:1]([C:7]1[C:8]([CH3:20])=[C:9]([CH3:19])[C:10]2[O:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][C:11]=2[CH:18]=1)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].C=O.Cl.[CH3:24]NC.Cl>CN(C)C=O.C(O)(=O)C>[CH2:24]=[C:2]([CH:3]([CH3:5])[CH3:4])[C:1]([C:7]1[C:8]([CH3:20])=[C:9]([CH3:19])[C:10]2[O:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][C:11]=2[CH:18]=1)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21568949HCID 21568949, compound

Product 1

HCID 21568960HCID 21568960, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5-isovaleryl-6,7-dimethylbenzofuran-2-carboxylic acid (8.5 g.), paraformaldehyde (2.0 g.), dimethylamine hydrochloride (3.3 g.) and acetic acid (1 ml.) is heated at 95°C. for 2.5 hours, treated with dimethylformamide (75 ml.), heated an additional 3.5 hours, poured into ice water (300 ml.) containing hydrochloric acid (5 ml.). The product is extracted into ether, washed with water, dried over magnesium sulfate, the solvent evaporated at reduced pressure to afford 5-(2-methyleneisovaleryl)-6,7-dimethylbenzofuran-2-carboxylic acid.

Workup

  1. temperatureheated an additional 3.5 hours
  2. extractionThe product is extracted into ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-a96ecd8d3e4f4c3b8d89cbe58c92dfed
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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