Hydrochloric Acid → HCID 21504771, compound

HRID 1288330Notes

Reaction equation

HRID 1288330 reaction equation
[CH3:1][C:2]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([CH3:17])([CH3:16])[O:7][C:6]=2[C:5]([C:18](=[O:20])[CH3:19])=[C:4]([OH:21])[CH:3]=1.[C:22](OCC)(=O)[C:23]([O:25]CC)=[O:24].[Na].Cl>C(O)C>[C:23]([C:22]1[O:21][C:4]2[CH:3]=[C:2]([CH3:1])[C:11]3[C:10]4[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=4[C:8]([CH3:17])([CH3:16])[O:7][C:6]=3[C:5]=2[C:18](=[O:20])[CH:19]=1)([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5360545SodiumHCID 12204713HCID 12204713, compound

Product 1

HCID 21504771HCID 21504771, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 1.2 gm (4.3 millimols) of 1-methyl-3-hydroxy-4-acetyl-6,6-dimethyl-6H-dibenzo-[b,d]-pyran and 1.2 gm (8.3 millimols) of diethyl oxalate in 10 ml of ethanol was poured at 40° C into a solution of 1.03 gm (45 millimols) of sodium in 20 ml of ethanol. The mixture was refluxed for 1 hour, cooled to 10° C and acidified with 2 N hydrochloric acid. The raw reaction product was extracted twice with 15 ml of ether each, the combined extracts were dried, and the solvent was evaporated. The orange residue was refluxed for 13/4hours in 18.2 ml of a mixture of acetic acid and hydrochloric acid (1.2 : 1), the reaction mixture was then cooled, and the precipitate formed thereby was recrystallized from ethanol. 1.1 gm (77% of theory) of the compound named in the heading, m.p. 231°-232° C, were obtained.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe raw reaction product
  3. extractionwas extracted twice with 15 ml of ether each, the combined extracts
  4. customwere dried
  5. customthe solvent was evaporated
  6. temperatureThe orange residue was refluxed for 13/4hours in 18.2 ml of a mixture of acetic acid and hydrochloric acid (1.2 : 1)
  7. temperaturethe reaction mixture was then cooled
  8. customthe precipitate formed
  9. customthereby was recrystallized from ethanol
  10. customwere obtained

Sources & evidence

ORD record
ord-be0c43b88b1f48179a5d4a16a094ad9d
Source dataset
uspto-grants-1976_10
Patent number
US03987186

Reaction notes

Loading…