Phosphoric Acid → HCID 18688937, compound

HRID 1871823Notes

Reaction equation

HRID 1871823 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(=O)(O)(O)O.OP=O.C(O[C:19]([CH2:21][O:22][C:23]([C:25]1[CH:26]=[C:27]([OH:36])[C:28]2[C:33]([CH:34]=1)=[CH:32][C:31]([CH3:35])=[CH:30][CH:29]=2)=[O:24])=O)C>O.C(Cl)Cl>[C:1]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:21]2[O:22][C:23](=[O:24])[C:25]3[CH:26]=[C:27]([OH:36])[C:28]4[C:33]([C:34]=3[CH:19]=2)=[CH:32][C:31]([CH3:35])=[CH:30][CH:29]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 1140TolueneHCID 22497phosphenous acidHCID 18688940HCID 18688940, compound

Product 1

HCID 18688937HCID 18688937, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

Toluene, 1000 milliliters (mL), heptanes, i.e., a C7 distillate having a boiling range of from 82 to 98° C., (1000 mL), methylene chloride (1000 mL), phosphoric acid, 20.0 grams of an 85 weight percent solution, 5.0 grams of hypophosphorus acid and 625.0 grams of 3-(ethoxycarbonyl)methoxycarbonyl-1-hydroxy-6-methylnaphthalene were added to a reaction flask. The reaction flask was a 5 liter four necked round bottom reactor equipped with an overhead mechanical stirrer, thermometer, electric heating mantle, heavier than water Barrett water trap, Fredrich's condenser and bottom outlet. The mixture was heated to reflux (~55° C.) and about 2 mL of water was removed. 1,1-Diphenyl-2-propyn-1-ol, 903.25 grams of a 61 weight percent solution in methylene chloride, was added to the reactor and the mixture was heated at reflux (~57° C.) for about 8 hours. The hot mixture was filtered to separate the insoluble desired product from the other products of reaction. The crystals were washed with 1 liter of a 1:1:2 mixture of toluene:heptanes:methylene chloride and dried to yield 144 grams of 2-diphenylmethyl-6-hydroxy-9-methyl-4-oxo-4H-naphtho[2,1-c]pyran.

Workup

  1. additionwere added to a reaction flask
  2. customequipped with an overhead mechanical stirrer
  3. temperatureThe mixture was heated
  4. customwas removed
  5. addition1,1-Diphenyl-2-propyn-1-ol, 903.25 grams of a 61 weight percent solution in methylene chloride, was added to the reactor
  6. temperaturethe mixture was heated
  7. temperatureat reflux (~57° C.) for about 8 hours
  8. filtrationThe hot mixture was filtered
  9. customto separate the insoluble desired product
  10. customfrom the other products of reaction
  11. washThe crystals were washed with 1 liter of a 1:1:2 mixture of toluene
  12. dry with materialheptanes:methylene chloride and dried

Sources & evidence

ORD record
ord-a5595123a6344e668026f3c23914cc3c
Source dataset
uspto-grants-2000_08
Patent number
US06106744

Reaction notes

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