Methyl Methacrylate → (E)-3-(2,6-dimethylphenyl)-2-methylacrylic acid methyl ester

HRID 13879

반응식

HRID 13879 반응식
Cl[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[C:10]([O:15][CH3:16])(=[O:14])[C:11]([CH3:13])=[CH2:12].C1(C(N)C2CCCCC2)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCOCC1>[CH3:16][O:15][C:10](=[O:14])/[C:11](/[CH3:13])=[CH:12]/[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9]

참가 물질

7

반응물 3

HCID 6658Methyl MethacrylateHCID 328851-Chloro-2,6-dimethylbenzeneHCID 10774245alpha-Cyclohexylcyclohexanemethanamine

생성물 1

HCID 66772813(E)-3-(2,6-dimethylphenyl)-2-methylacrylic acid methyl ester수율 75.8%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 23136663Tri-tert-butylphosphonium Tetraphenylborate촉매HCID 312751,4-Dioxane용매

실험 절차

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.703 g (5 mmol) of 2-chloro-meta-xylene, 1.001 g (10 mmol) of methyl methacrylate, 0.034 g (0.038 mmol) of tris(dibenzylideneacetone)dipalladium (0), 1.074 g (5.5 mmol) of dicyclohexylmethylamine and 5 ml of 1,4-dioxane were weighed in the flask, followed by stirring. Further, 0.078 g (0.15 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 120° C. for 37 hours. After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.774 g of (E)-3-(2,6-dimethylphenyl)-2-methylacrylic acid methyl ester (yield: 76 mol % based on 2-chloro-meta-xylene). The identification of the product was made by 1H-NMR and 13C-NMR.

후처리

  1. customA 30-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 120° C. for 37 hours
  5. customAfter the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution
  6. additionwere added
  7. customfollowed by separation
  8. customThe organic phase was purified by column chromatography

출처 및 근거

ORD 기록
ord-eaead8a88a534c838a126946e0fc6db1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728176B2

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