Hydrochloric Acid → HCID 21568945, compound

HRID 1579621Notes

Reaction equation

HRID 1579621 reaction equation
[C:1]([C:7]1[C:8]([CH3:20])=[C:9]([CH3:19])[C:10]2[O:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][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][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][C:11]=2[CH:18]=1)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 21568946HCID 21568946, compound

Product 1

HCID 21568945HCID 21568945, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture 2,3-dihydro-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° for 2.5 hours, treated with dimethylformamide (75 ml.), heated an additional 3.5 hours then poured into ice water (300 ml.) containing hydrochloric acid (5 ml.). The product is extracted into ether, washed with water, dried over magnesium sulfate and the solvent evaporated at reduced pressure to afford 2,3-dihydro-5-(2-methyleneisovaleryl)-6,7-dimethylbenzofuran-2-carboxylic acid which melts at 97°C. after recrystallization from cyclohexane.

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-139f6ed7f4d0434fa876e640dbe90033
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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