Lithium hydroxide, monohydrate → 4-(4-(2-Tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid

HRID 1927746Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=[C:10]([C:25]#[N:26])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O>O1CCOCC1.Cl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[C:10]([C:25]#[N:26])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 10 °C

Procedure

Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate (11.60 g, 31.57 mmol) was dissolved in dioxane (160 mL) and the solution was cooled to 10° C. in an ice bath. LiOH—H2O, 1M (37.89 ml, 37.89 mmol) was added to the solution and the mixture was stirred at ambient temperature for 5 hours. The mixture was diluted with 2N HCl (100 mL) and CH2Cl2 (200 mL). Layers were separated and aqueous layer was extracted with CH2Cl2. The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered through a Celite pad and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to provide 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid (7.29 g) as a white solid.

Workup

customLayers were separated
extractionaqueous layer was extracted with CH2Cl2
washThe combined extracts were washed with brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered through a Celite pad
concentrationconcentrated under reduced pressure
customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record: ord-1613f41ac3cf4e86a559144808623edb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183289B2

Reaction notes

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