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

HRID 33989Notes

Reaction equation

HRID 33989 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

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.

Workup

  1. filtrationThe resulting yellow precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-cabf27434a594b5eb6fa71973f4004b7
Source dataset
uspto-grants-2008_09
Patent number
US07429658B2

Reaction notes

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