تفاعل #1959005

معادلة التفاعل

Toluene

phosphoric acid

hypophosphorus acid

3-(ethoxycarbonyl)methoxycarbonyl-1-hydroxy-6-methylnaphthalene

→

2-diphenylmethyl-6-hydroxy-9-methyl-4-oxo-4H-naphtho[2,1-c]pyran

المذيبات

water

water

methylene chloride

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added to a reaction flask
2. 2
   أخرىequipped with an overhead mechanical stirrer
3. 3
   درجة الحرارةThe mixture was heated
4. 4
   أخرىwas removed
5. 5
   workup.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. 6
   درجة الحرارةthe mixture was heated
7. 7
   درجة الحرارةat reflux (~57° C.) for about 8 hours
8. 8
   ترشيحThe hot mixture was filtered
9. 9
   أخرىto separate the insoluble desired product
10. 10
    أخرىfrom the other products of reaction
11. 11
    غسيلThe crystals were washed with 1 liter of a 1:1:2 mixture of toluene
12. 12
    تجفيفheptanes:methylene chloride and dried

الإجراء التجريبي

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.

المصدر