Hydrochloric Acid → HCID 21504764, compound

HRID 1288328Notes

Reaction equation

HRID 1288328 reaction equation
[Cl:1][C:2]1[C:15]([OH:16])=[CH:14][C:5]2[O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:4]=2[CH:3]=1.[C:17]([C:23](OC)=[O:24])#[C:18][C:19]([O:21]C)=[O:20].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+].Cl>O1CCOCC1.O>[C:19]([C:18]1[O:16][C:15]2[C:2]([Cl:1])=[CH:3][C:4]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[CH2:7][O:6][C:5]=3[C:14]=2[C:23](=[O:24])[CH:17]=1)([OH:21])=[O:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 12980Dimethyl acetylenedicarboxylateHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 21504768HCID 21504768, compound

Product 1

HCID 21504764HCID 21504764, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

The starting compound was obtained in the following way: A solution of 9.8 gm (0.04 mol) of 2-chloro-3-hydroxy6H-dibenzo-[b,d]-pyran and 9.0 gm (0.06 mol) of dimethyl acetylene-dicarboxylate in 20 ml of dioxane was admixed with 0.85 ml of a 40% solution of benzyl trimethylammonium hydroxide in water. The resulting solution was heated for 10 minutes at 75° C, then cooled, admixed with 5 N sodium hydroxide, and heated for one hour more. Then, the reaction mixture was cooled, acidified with concentrated hydrochloric acid, and the precipitate formed thereby was filtered off, washed with water, dried and recrystallized from a mixture of acetic acid and chloroform (1:9). The compound named in the heading, m.p. 242°-243° C, was obtained with a yield of 10.5 gm (99%) of theory).

Workup

  1. customThe starting compound was obtained in the following way
  2. temperaturecooled
  3. temperatureheated for one hour more
  4. temperatureThen, the reaction mixture was cooled
  5. customthe precipitate formed
  6. filtrationthereby was filtered off
  7. washwashed with water
  8. customdried
  9. customrecrystallized from a mixture of acetic acid and chloroform (1:9)
  10. customwas obtained with a yield of 10.5 gm (99%) of theory)

Sources & evidence

ORD record
ord-c30e0f875f954764abcb2d9b3e7cb333
Source dataset
uspto-grants-1976_10
Patent number
US03987186

Reaction notes

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