Phenetole → 1-Ethoxycyclohexa-1,4-diene

A solution of 59.5 g. of phenetole (ethyl phenyl ether) in 200 ml. of dry ether and 800 ml. of liquid ammonia which was distilled from sodium was placed in a 2 1. three necked flask fitted with a mechanical agitator, dry ice condenser and dropping funnel and cooled with a dry ice - ethyl alcohol bath. To this mixture was added 14.1 g. of lithium wire in small pieces. After the addition was complete, absolute ethyl alcohol (about 400 ml.) was added until the blue color disappeared. The resulting mixture was left in a good exhaust hood for the ammonia to evaporate. Water (200 ml.) was cautiously added to the resulting mixture and the precipitate filtered off. The organic layer was separated and the water layer extracted three times with 50 ml. of ether. The combined organic solutions were washed neutral with water and dried over anhydrous potassium carbonate. The solvent was removed by atmospheric distillation through a 37 cm. column packed with glass helices. There was produced 45 g. (75% of theory). This material analyzed as 86% 1-ethoxy-1,3-cyclohexadiene.

1. distillationof liquid ammonia which was distilled from sodium
2. customthree necked flask fitted with a mechanical agitator, dry ice condenser
3. temperaturecooled with a dry ice - ethyl alcohol bath
4. additionTo this mixture was added 14.1 g
5. additionAfter the addition
6. additionabsolute ethyl alcohol (about 400 ml.) was added until the blue color
7. waitThe resulting mixture was left in a good exhaust hood for the ammonia
8. customto evaporate
9. additionWater (200 ml.) was cautiously added to the resulting mixture
10. filtrationthe precipitate filtered off
11. customThe organic layer was separated
12. extractionthe water layer extracted three times with 50 ml
13. washThe combined organic solutions were washed neutral with water
14. dry with materialdried over anhydrous potassium carbonate
15. customThe solvent was removed by atmospheric distillation through a 37 cm
16. customThere was produced 45 g

ORD record

ord-cddd44d960164fba8f2284b9d8253697

Source dataset

uspto-grants-1976_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03962354