Sodium Bicarbonate → 5-(4-Fluorophenoxy)isophthalic acid

HRID 1889645Notes

Reaction equation

[F:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:17]([O:19]C)=[O:18])[CH:10]=[C:11]([CH:16]=2)[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CO.O>[F:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:16]=[C:11]([C:12]([OH:14])=[O:13])[CH:10]=[C:9]([CH:8]=2)[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of dimethyl 5-(4-fluorophenoxy)isophthalate (3.8 g, 12.49 mmol) and sodium bicarbonate (1.2 g, 14.28 mmol) in MeOH (100 mL) and water (15 mL) was heated at 80° C. overnight. An additional 500 mg of sodium bicarbonate was added to the reaction mixture and continued to heat at 100° C. for 6 h. HPLC showed a mixture of monoacid (major), diacid (minor) and a small amount of starting material. Prep HPLC provided diacid, 5-(4-fluorophenoxy)isophthalic acid (0.4 g, 1.448 mmol, 11.60% yield) and monoacid, 3-(4-fluorophenoxy)-5-(methoxycarbonyl)benzoic acid (2.2 g, 7.58 mmol, 60.7% yield) as a white solid.

Workup

temperatureto heat at 100° C. for 6 h

Sources & evidence

ORD record: ord-ae506443b61f419db218e93b5a0e33f3
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501992B2

Reaction notes

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