Lithium hydroxide, monohydrate → 4-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyric acid

HRID 1976809Notes

Reaction equation

HRID 1976809 reaction equation
[OH:1][CH:2]([C:4]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])=[C:6]([O:21][CH3:22])[CH:5]=1)[CH3:3].O.[OH-].[Li+]>CO>[OH:1][CH:2]([C:4]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:6]([O:21][CH3:22])[CH:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10591264Methyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyrate

Product 1

HCID 34372874-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyrate (5.04 g) from above was stirred with lithium hydroxide monohydrate in methanol using conventional protocols. 4-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butyric acid was obtained as an amorphous yellow solid (4.0 g, 83%). 1H NMR (CDCl3) δ 1.34 (3H, d, J=11 Hz, MeCOH), 2.03 (2H, m, CCH2C), 2.38 (2H, t, J=7.3 Hz, CH2CO), 3.81 (3H, s, OMe), 3.96 (2H, t, J=7.4 Hz, CH2O), 4.13 (2H, brs, OH), 5.38 (1H, q, J=10.8 Hz, CHOH), 7.19 (1H, s, aromatic, and 7.43 (1H, s, aromatic).

Sources & evidence

ORD record
ord-b3fe6ddd638f4b13a66731c32803e84c
Source dataset
uspto-grants-2001_05
Patent number
US06228988B1

Reaction notes

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