Hydrochloric Acid → 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-isopropoxy-benzoic Acid

HRID 1831816Notes

Reaction equation

C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([CH3:14])[CH3:13])=[C:7]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH:6]=1)C.O.[OH-].[Na+].Cl>O1CCOCC1>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[CH2:17][CH2:16][O:15][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:4]([OH:26])=[O:3]

Participants

Conditions

Temperature: 60 °C

Procedure

0.75 g (1.89 mmol) of 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-isopropoxy-benzoic acid ethyl ester was dissolved in 15 ml of dioxan. 5 ml of water and 2N aqueous NaOH was added to the solution to give a pH of 13. The reaction solution was heated at 60° C. for 4 h and stirred at room temperature for 16 h. The reaction solution was cooled to 0° C. and concentrated hydrochloric acid was added to give a pH of 1–2, whereupon the product precipitated from solution. The suspension was stirred for 30 min, then the product was filtered off and dried under reduced pressure.

Workup

customto give a pH of 13
temperatureThe reaction solution was cooled to 0° C.
customto give a pH of 1–2
customwhereupon the product precipitated from solution
stirringThe suspension was stirred for 30 min
filtrationthe product was filtered off
customdried under reduced pressure

Sources & evidence

ORD record: ord-3d8a8ad4a71c4289852ee17cc0e5fb0b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067665B2

Reaction notes

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