Hydrochloric Acid → Methyl 2-(4-isobutyrylphenoxy)acetate

HRID 646215

반응식

HRID 646215 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[CH:6]([CH3:8])[CH3:7].[CH3:11][O:12][C:13]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].Cl>CCCCCC.C(OCC)(=O)C>[C:5]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:13]([O:12][CH3:11])=[O:14])=[CH:18][CH:19]=1)(=[O:9])[CH:6]([CH3:8])[CH3:7]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 16365Methyl phenoxyacetateHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 12797090Methyl 2-(4-isobutyrylphenoxy)acetate

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To an oven-dried round bottom flask was added anhydrous AlCl3 (24.1 g, 0.18 mol), which was subsequently purged with Ar. Methylene chloride (10 mL) was added via syringe and the resulting slurry was cooled to 0° C. in an ice bath. The isobutryl chloride (6.9 mL, 6.6×10−2 mol) was added dropwise via syringe. The methyl phenoxy acetate (8.7 mL, 6.0×10−2 mol) was added dropwise via syringe. The reaction was stirred until deemed complete by thin layer chromatography (TLC) (25% ethyl acetate in hexane) (approximately 2 h). The reaction mixture was poured slowly into a mixture of ice (100 g) and concentrated HCl (40 mL). The organic layer was separated and the organic layer extracted with methylene chloride (3×100 mL). The combined organic layers were washed with water (3×100 mL) and dried over MgSO4. The solvent was removed in vacuo to reveal 14 g of a white, crystalline solid (quantitative yield). 1H NMR (300 NMR, CDCl3) δ7.97 (2H, d, J=8.9 Hz), 6.96 (2H, J=8.9 Hz), 4.71 (2H, s), 3.82 (3H, s), 3.51 (1H, septet, J=6.8 Hz), 1.22 (6H, d, J=6.8 Hz).

후처리

  1. customwas subsequently purged with Ar
  2. additionMethylene chloride (10 mL) was added via syringe
  3. customThe organic layer was separated
  4. extractionthe organic layer extracted with methylene chloride (3×100 mL)
  5. washThe combined organic layers were washed with water (3×100 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-046a7f7af1ad4bf9b8aaee2407ce74b2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705065B2

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