Hydrochloric Acid → (E)-2-(4-(methoxymethoxy)phenyl)-3-o-tolylpent-2-enoic acid

HRID 884069Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2a (240 mg, 0.677 mmol) in MeOH (7 ml) was added 2N NaOH (3.4 ml) and the mixture was stirred at 80° C. for 18 h. After cooling, 2 N HCl (3.4 ml) was added drop wise under ice cooling, and the whole was extracted with AcOEt, the organic layer was washed with brine, dried over Na2SO4, then concentrated. The residual solid was triturated with hexanes to give 3a (79%). 3a: colorless powder; 1H-NMR (CDCl3) δ 1.05 (3H, t, J=7.5 Hz), 2.08 (3H, s), 2.68 (1H, m), 2.77 (1H, m), 3.41 (3H, s), 5.07 (2H, s), 6.75 (2H, d, J=8.7 Hz), 6.93 (2H, d, J=8.7 Hz), 7.01 (2H, m), 7.05-7.09 (3H, m).

Workup

temperatureAfter cooling
extractionthe whole was extracted with AcOEt
washthe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residual solid was triturated with hexanes

Sources & evidence

ORD record: ord-27ad2c00410b458c961e79cecdbcfdbd
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236987B2

Reaction notes

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