4-Nitrophenol → Ethyl 2-(4-nitrophenoxy)acetate

HRID 54980

반응식

HRID 54980 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 9804-NitrophenolHCID 7751Ethyl chloroacetateHCID 11430Potassium Carbonate

생성물 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetate수율 73.3%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6342Acetonitrile용매

실험 절차

The product was made by procedures which are well known in the art, that is, by alkylation of 4-nitrophenol (29.2 g, 0.21 mol) with ethyl chloroacetate (24.5 g, 0.20 mole) in the presence of potassium carbonate (30.4 g, 0.22 mol), potassium iodide (0.5 g) and acetonitrile (150 mL) to afford ethyl 4-nitrophenoxyacetate (33 g, 73.3%), m.p. 75°-76° C. after recrystallization from tert-butylmethyl ether; hydrogenation of the latter (22.5 g) at 50 psi in ethyl acetate (200 mL) in the presence of 10% palladium on Carbon (0.3 g) to afford 22.5 g (97%) of ethyl 4-aminophenoxyacetate, m.p. 157°-158° C.; and treatment of the latter (18.52 g, 0.08 mol) with methanesulfonyl chloride (12.6 g, 0.11 mol) in CH2Cl2 (250 mL) in the presence of pyridine (35 mL) to afford N-[4-(ethoxycarbonylmethoxy)phenyl]methanesulfonamide, 20.06 g (92%), m.p. 77.3°-78.5° C. after recrystallization from ethanol.

출처 및 근거

ORD 기록
ord-8ca84b6c8a5f4c9ea78b35e1dc641c25
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624922

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