(RS)-Naproxen methyl ester → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 1719807

반응식

HRID 1719807 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])[CH:7]=[CH:6]2.CO.[OH-].[K+].O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:18])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2

참가 물질

4

반응물 2

HCID 529084(RS)-Naproxen methyl esterHCID 86591755KOH MeOH Water

생성물 1

HCID 13022-(6-Methoxy-2-naphthyl)propionic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

The oil, 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate, from Example 6 and 4.9 g of sodium acetate is dissolved in 200 ml of glacial acetic acid. The mixture is heated to 90°-100° C. and maintained at that temperature for approximately 3 hours. An additional 3.8 g of sodium acetate is added to the reaction mixture and the mixture is stirred for an additional three hours. The reaction mixture then is heated to 100° C. where it is held for an additional three hours. After that time 200 ml of methylene chloride and 50 ml of water is added to the reaction mixture. The organic and aqeuous layers are separated and the organic layer is evaporated under reduced pressure to afford methyl 2-(6-methoxy-2-naphthyl)propionate. The resulting methyl 2-(6-methoxy-2-naphthyl)propionate is hydrolyzed with a mixture of methanol/potassium hydroxide-water. The reaction mixture is poured into water and extracted with methylene chloride to afford the acid, 2-(6-methoxy-2-naphthyl)propionic acid (melting point: 153°-155° C.).

후처리

  1. extractionextracted with methylene chloride

출처 및 근거

ORD 기록
ord-22ef706eb05a4247ac6b9ebebd0e7db9
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04542237

연결된 노트

불러오는 중…