Hydrochloric Acid → 4-[4-(Hydroxymethyl)-2-methoxy-5-nitrophenoxy]butanoic acid

HRID 33989노트

반응식

HRID 33989 반응식
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([CH2:17][OH:18])=[CH:10][C:9]=1[O:19][CH3:20].[OH-].[Na+].O.Cl>CO.C(Cl)(Cl)Cl.C(O)(=O)C>[OH:18][CH2:17][C:11]1[C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]([O:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[C:9]([O:19][CH3:20])[CH:10]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15334312Methyl 4-[4-(hydroxymethyl)-2-methoxy-5-nitrophenoxy]butanoate

생성물 1

HCID 42753554-[4-(Hydroxymethyl)-2-methoxy-5-nitrophenoxy]butanoic acid수율 90.1%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 6212Chloroform용매

실험 절차

A solution of the ester (50)(10.00 g, 33.4 mmol) in methanol (100 mL) was added dropwise to a stirring solution of 1M NaOH (100 mL) and H2O (50 mL). TLC (1:10:100 Acetic acid: MeOH: CHCl3) after 16 hours revealed the complete loss of starting material. The solution was acidified to pH1 with conc. HCl. The resulting yellow precipitate was collected by vacuum filtration to provide the product (51) as a yellow solid (8.58 g, 90%). MP=172-175° C. 1H NMR (250 MHz, CDCl3) δ 7.71 (s, 1H), 7.40 (s, 1H), 4.99 (s, 2H), 4.13 (t, J=6.3 Hz, 2H), 3.98 (s, 3H), 2.52 (t, J=7.1 Hz, 2H), 2.15 (pent, J=6.7 Hz, 2H). 13C NMR (67.8 MHz, CDCl3) 174.5 (C12), 154.2 (Cquat.), 146.4 (Cquat.), 138.5 (Cquat.), 134.7 (Cquat.), 109.8 (C6), 109.3 (C3), 68.3 (C9), 60.9 (C1), 56.2 (C8), 30.2 (C11), 24.3 (C10). IR (cm−1) 3533, 2976, 2634, 1709, 1617, 1577, 1520, 1411, 1286, 1214, 1019, 990, 888, 876, 814, 756, 677. MS (M+ —OH) 268.0. Anal. Calcd for C12H15NO7: C, 50.53; H, 5.30; N, 4.91. Found: C, 50.48; H, 5.22; N, 4.88.

후처리

  1. filtrationThe resulting yellow precipitate was collected by vacuum filtration

출처 및 근거

ORD 기록
ord-cabf27434a594b5eb6fa71973f4004b7
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429658B2

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