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

HRID 453515노트

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HRID 453515 반응식
[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]

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 68466372Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate

생성물 1

HCID 684683974-(4-(2-Tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid수율 65.3%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
10 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5d38aa6cbc734074b97d78efcdf90125
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492437B2

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