Hydroxyphenylacetic acid → 3-[((4-Chloroanilino)carbonyl)methyl]phenol

HRID 582940

반응식

HRID 582940 반응식
[CH3:1][C:2]([CH3:4])=[O:3].[OH:5][C:6]1C=[CH:10][C:9](CC(O)=O)=[CH:8][CH:7]=1.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=C(C)C=C(C)C=1.C(C(CC)=O)C>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:6]([CH2:7][C:8]2[CH:1]=[C:2]([OH:3])[CH:4]=[CH:10][CH:9]=2)=[O:5])=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 127Hydroxyphenylacetic acidHCID 180AcetoneHCID 78124-ChloroanilineHCID 24819Phosphorus pentachloride

생성물 1

HCID 234407563-[((4-Chloroanilino)carbonyl)methyl]phenol수율 90%

시약·촉매·용매 2

HCID 7288Ethyl ketone용매HCID 7947Mesitylene용매

실험 절차

FIG. 6b presents a similar reaction scheme to FIG. 6a, except that 3- rather than 4-hydroxyphenylacetic acid (HPAA) is used as the precursor material so that the final compound has a meta rather than a para substitution. In addition, rather than reacting with acetone (dimethyl ketone) a diethyl ketone is used to position ethyl, rather than methyl, moieties in the group substituted on one of the phenyl rings. By example, 1.5 g (10 mmol) 3-HPAA and 2.6 g (20 mmol) 4-chloroaniline in 20 ml of mesitylene was heated to reflux. Then 0.33 g (2.55 mmol) PCl5 was then slowly added to the above refluxing solution and the refluxing was continued for two hours. The reaction mixture was then cooled and then worked up as described above to yield 2.2 g (90% yield) of 3-[((4-chloroanilino) carbonyl)methyl]phenol. As described above, chloroform (0.8 ml) was added to a stirred and ice-cooled mixture of 1.23 grams of 3-[((4-chloroanilino)carbonyl)methyl]phenol and 1.6 g NaOH in 15 ml of acetone. The reaction mixture was allowed to warm to room temperature and stirring continued for an additional 10 hours. The usual work-up yielded 2-[3-[((4-chloroanalino)carbonyl) methyl)]phenoxy]-2-methylpropionic acid as a low temperature melting sticky solid (C,H,Cl,N analysis yielded (C18H18ClNO4); NMR δPPM: 1.42 (6H, s, CH3), 3.61 (2H, s, benzylic CH2), and 6.6-7.75 (8H, m, aromatic H)). However, rather than using acetone as the reaction solvent, diethylketone can be used in the same manner as described above to yield the butanoic acid (as opposed to propanoic acid) structure shown in FIG. 6b.

후처리

  1. temperatureThe reaction mixture was then cooled

출처 및 근거

ORD 기록
ord-57f0a90694974a49b170a0b3cfe0eb9a
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05927283

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