Lithium Hydroxide → [5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-acetic acid

HRID 1955255Notes

Reaction equation

C(OC(=O)[C:5](=[O:27])[CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=[CH:9][C:8]=1[N+:24]([O-:26])=[O:25])C.[OH-:29].[Li+]>CO>[CH2:17]([O:16][CH2:15][CH2:14][O:13][C:11]1[CH:10]=[CH:9][C:8]([N+:24]([O-:26])=[O:25])=[C:7]([CH2:6][C:5]([OH:27])=[O:29])[CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 3-[5-(2-benzyloxy-ethoxy)-2-nitro-phenyl]-2-oxo-propionic acid ethyl ester(37.77 g, 97.50 mmol) in methanol (370 ml) was added 1 N lithium hydroxide solution (230 ml, 0.23 mol). The deep red reaction mixture was stirred at 55° C. for 30 min and worked up to give [5-(2-benzyloxy-ethoxy)-2-nitro-phenyl]-acetic acid (22.42 g, 69%) as an off-white solid. Analysis calculated for C17H17NO6 : C, 61.63; H, 5.17; N, 4.23. Found: C, 61.66; H, 5.08; N, 4.18.

Workup

customThe deep red reaction mixture

Sources & evidence

ORD record: ord-9e077d8914e340978b2cb5be20890a90
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124323

Reaction notes

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