Hydrochloric Acid → HCID 21504777, compound

HRID 1288333Notes

Reaction equation

HRID 1288333 reaction equation
[CH3:1][C:2]1[C:17]([OH:18])=[CH:16][C:5]2[O:6][C:7]([CH3:15])([CH3:14])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:4]=2[CH:3]=1.[C:19]([C:25]([O:27]C)=O)#[C:20][C:21]([O:23]C)=[O:22].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+].Cl.[S:44](=O)(=[O:47])([OH:46])[OH:45]>O1CCOCC1.O>[C:21]([C:20]1[O:18][C:17]2[C:2]([CH3:1])=[CH:3][C:4]3[C:9]4[CH:10]=[CH:11][C:12]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:13][C:8]=4[C:7]([CH3:15])([CH3:14])[O:6][C:5]=3[C:16]=2[C:25](=[O:27])[CH:19]=1)([OH:23])=[O:22]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 12980Dimethyl acetylenedicarboxylateHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 21504760HCID 21504760, compound

Product 1

HCID 21504777HCID 21504777, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 17 gm (0.07 mol) of 2,6,6-trimethyl3-hydroxy-6H-dibenzo-[b,d]-pyran and 14.2 gm (0.1 mol) of dimethyl acetylene-dicarboxylate in 40 ml of dioxane was admixed with a 40% solution of benzyl trimethylammonium hydroxide in water. The mixed solution was heated at 80° C for 30 minutes, cooled, admixed with 50 ml of 5 N sodium hydroxide and again heated for 1 hour at 80° C. Then, the reaction mixture was cooled, acidified with concentrated hydrochloric acid and extracted with ether. The ether extract was dried and evaporated, and the oily residue thus obtained was added slowly at room temperature to 150 ml of concentrated sulfuric acid. After standing for 1 day at room temperature, the solution was poured into ice water, and the precipitated solid substance was filtered off and heated for 3 hours in a mixture of 25 ml of acetic acid and 10 ml of concentrated hydrochloric acid. Subsequently, the mixture was evaporated to dryness, and the residue was recrystallized from methanol, yielding the compound named in the heading in the form of reddish crystals, m.p. 264°-266° C (hemihydrate).

Workup

  1. temperaturecooled
  2. temperatureagain heated for 1 hour at 80° C
  3. temperatureThen, the reaction mixture was cooled
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. customwas dried
  7. customevaporated
  8. customthe oily residue thus obtained
  9. filtrationthe precipitated solid substance was filtered off
  10. temperatureheated for 3 hours in a mixture of 25 ml of acetic acid and 10 ml of concentrated hydrochloric acid
  11. customSubsequently, the mixture was evaporated to dryness
  12. customthe residue was recrystallized from methanol
  13. customyielding the compound

Sources & evidence

ORD record
ord-352792cff84f4de0a7aa5b090f67ad59
Source dataset
uspto-grants-1976_10
Patent number
US03987186

Reaction notes

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