Hydroquinone → Ketoethyl methacrylate

HRID 526803

반응식

HRID 526803 반응식
[C:1]1(C=CC(O)=C[CH:3]=1)[OH:2].[C:9]1(N2CCC(=O)N2)[CH:14]=CC=C[CH:10]=1.P(=O)(O)(O)O.[C:26](=[O:29])([O-])[OH:27].[Na+]>O>[C:26]([O:27][CH2:3][CH:1]=[O:2])(=[O:29])[C:9]([CH3:14])=[CH2:10]

참가 물질

6

반응물 4

HCID 785HydroquinoneHCID 1004Phosphoric AcidHCID 7090PhenidoneHCID 516892Sodium Bicarbonate

생성물 1

HCID 22134245Ketoethyl methacrylate수율 27.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In a 2 L four-necked flask, 180 g of potassium methacrylate (made by Wako Pure Chemical Industries Ltd., purity: 98.0%) was put, and 900 g of N,N-dimethylformamide was added thereto, and a stirrer, a thermometer and a Dimroth cooling tube were connected thereto. Then, 308 g of 2-bromo-1,1-diethoxyethane (made by ALDRICH Corporation, purity: 97%), 0.9 g of p-methoxyphenol and 1.32 g of tetramethylammonium iodide were added thereto, and the resulting mixture was allowed to react for 2 hours at 150° C. under stirring. The reaction mixture was cooled to room temperature, a precipitate was separated by filtration, and then N,N-dimethylformamide was distilled off, and the resulting product was distilled under reduced pressure to obtain 174 g of a reaction product (GC purity: 98.5%). From the thus obtained reaction product, 19 g was put into a 1 L four-necked flask subjected to replacement with nitrogen, stirred and dispersed into 430 mL of water, and 0.21 g of hydroquinone, 0.41 g of 1-phenyl-3-pyrazolidinone (made by Tokyo Kasei Kogyo Co., Ltd., purity: 98.0% or more) and 2.8 g of 85% phosphoric acid were added thereto, and the resulting mixture was allowed to react at 70 to 80° C. for 3 hours under stirring. The reaction mixture was cooled to room temperature, and neutralized using a 10% sodium hydrogen carbonate aqueous solution, and repeatedly extracted with diethyl ether. An organic layer was dried over magnesium sulfate, separated by filtration, and distilled under reduced pressure to give 5.6 g of 2-oxoethyl methacrylate (yield: 27.6% based on potassium methacrylate).

후처리

  1. customFrom the thus obtained reaction product, 19 g
  2. customwas put into a 1 L four-necked flask
  3. additionwere added
  4. customto react at 70 to 80° C. for 3 hours
  5. stirringunder stirring
  6. extractionrepeatedly extracted with diethyl ether
  7. dry with materialAn organic layer was dried over magnesium sulfate
  8. customseparated by filtration
  9. distillationdistilled under reduced pressure

출처 및 근거

ORD 기록
ord-cd89f54a9d1d4d208263341381c2da9f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346775B2

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