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

HRID 33989ノート

反応式

HRID 33989 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒2 回HCID 6212Chloroform溶媒

実験手順

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.

後処理

  1. filtrationThe resulting yellow precipitate was collected by vacuum filtration

出典と根拠

ORDレコード
ord-cabf27434a594b5eb6fa71973f4004b7
出典データセット
uspto-grants-2008_09
特許番号
US07429658B2

反応ノート

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