Hydrochloric Acid → [(4-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]acetic acid

HRID 1992982Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.CCO.[OH-].[Na+].Cl>C1COCC1>[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:4]([O:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl [(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]acetate (234) (0.170 g, 0.39 mmol) was dissolved in 1:1 THF:EtOH (6 mL). To the above mixture was added 1 N NaOH (0.5 mL) at room temperature and heated to 50° C. The reaction mixture was kept at that temperature for 0.5 h and cooled at RT. Reaction mixture was acidified with 25% aqueous HCl, and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated under reduced pressure to afford 0.155 g (97%) the crude product (235). 1H NMR (400 MHz, CDCl3): δ 7.78 (d, J=10.0 Hz, 1H), 7.54 (s, 1H), 7.28-7.03 (m, 4H), 6.64 (d, J=9.0 Hz, 2H), 6.50 (d, J=8.9 Hz, 2H), 4.54 (s, 2H), 3.93 (s, 3H), 2.23 (s, 3H).

Workup

temperaturecooled at RT
customReaction mixture
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-54f47fb08a3b4c15b83e8b95f82bbc01
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649093B2

Reaction notes

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