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

HRID 54980

反応式

HRID 54980 の反応式
[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]

参加物

6

反応物 3

HCID 9804-NitrophenolHCID 7751Ethyl chloroacetateHCID 11430Potassium Carbonate

生成物 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetate収率 73.3%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 6342Acetonitrile溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-8ca84b6c8a5f4c9ea78b35e1dc641c25
出典データセット
uspto-grants-1997_04
特許番号
US05624922

関連ノート

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