Hydrochloric Acid → 4-Chloro-3-[2-(4-methoxy-phenyl)-ethoxy]-benzoic Acid

HRID 1831823Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

1.27 g (3.96 mmol) of 4-Chloro-3-[2-(4-methoxy-phenyl)-ethoxy]-benzoic acid methyl 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 2 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-71bb0a440b9f4fec81a77d0dc236702f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067665B2

Reaction notes

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