Sodium Hydroxide → 2-(2,5-Dichloro-4-methoxyphenyl)acetic acid

HRID 1930122

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([Cl:10])=[CH:4][C:3]=1[CH:11](C(OCC)=O)[C:12]([O:14]CC)=[O:13].[OH-].[Na+]>C1COCC1.CCO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([Cl:10])=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of diethyl 2-(2,5-dichloro-4-methoxyphenyl)malonate (Intermediate 4-5; 1.88 g, 5.61 mmol) in THF (55 mL) and EtOH (5 mL) was treated with 2M sodium hydroxide (11.22 mL, 22.44 mmol) in one portion and the resulting solution was stirred at 60° C. for 17 hours. The reaction mixture was evaporated and the aqueous residue was acidified with 2M HCl. The precipitate was collected by filtration, washed with water (25 mL) and dried under vacuum to afford 2-(2,5-dichloro-4-methoxyphenyl)acetic acid (0.800 g, 60.7%) as a grey solid, which was used without further purification.

Workup

customThe reaction mixture was evaporated
filtrationThe precipitate was collected by filtration
washwashed with water (25 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-1c6b304e486b48c9804a207ee40507f9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188092B2

Linked notes

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