반응 #450994

반응 방정식

toluene

(S)-2-(6-methoxy-2-naphthyl)propionic acid

racemic 2-(6-methoxy-2-naphthyl)propionic acid

NaOH

→

sodium (S)-2-(6-methoxy-2-naphthyl)propionate

2-(6-methoxy-2-naphthyl)propionic acid

수율 91.6%

용매

Water

water

반응 조건

후처리

1. 1
   기타Two clear liquid phases were obtained
2. 2
   기타The total amount of water collected during the strip
3. 3
   기타the amount of toluene removed
4. 4
   온도cooled to 75° C. in 82 minutes
5. 5
   workup.STIRRINGagitated at 75° C. for 60 minutes
6. 6
   기타settled well at the end of the 60-minute 75° C. ride
7. 7
   세척The centrifuge cake (sodium (S)-2-(6-methoxy-2-naphthyl)propionate monohydrate) was washed with 149.94 grams of hot (75° C.) toluene
8. 8
   세척Totals of 483.77 and 127.61 grams of mother liquor and wash liquor
9. 9
   기타were recovered
10. 10
    기타after drying for 8 hours at 80°-90° C. and under full vacuum

실험 절차

Using the apparatus of the above Comparative Example, a toluene solution of 2-(6-methoxy-2-naphthyl)propionic acid (580.68 grams, 18.11 wt % solids, 91.64% S-enantiomer) was prepared from a sample of high chiral purity (S)-2-(6-methoxy-2-naphthyl)propionic acid, and racemic 2-(6-methoxy-2-naphthyl)propionic acid. The solution was heated to 85° C. Totals of 27.59 grams of 49.22 wt % NaOH and 7.822 grams of water were added. Two clear liquid phases were obtained. Water was stripped to 94.0° C. in 285 minutes. The total amount of water collected during the strip was 21.36 grams and the amount of toluene removed was 1.83 grams. The batch was agitated at 93.6°-94.0° C. for 15 minutes and cooled to 75° C. in 82 minutes and agitated at 75° C. for 60 minutes. Solids in the slurry settled well at the end of the 60-minute 75° C. ride. The centrifuge cake (sodium (S)-2-(6-methoxy-2-naphthyl)propionate monohydrate) was washed with 149.94 grams of hot (75° C.) toluene. Totals of 483.77 and 127.61 grams of mother liquor and wash liquor were recovered, respectively. The wet centrifuge cake weighed 75.02 grams which after drying for 8 hours at 80°-90° C. and under full vacuum yielded 67.29 grams of anhydrous sodium (S)-2-(6-methoxy-2-naphthyl)propionate. Chiral purities for the product and the mother liquor were found by analysis to be 99.03% S-enantiomer and 80.28% S-enantiomer, respectively.

출처