Ammonium Chloride → Methyl 2-methoxymethylphenylglyoxylate

HRID 36603

반응식

HRID 36603 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][CH3:11].[Cl-].[CH3:13][O:14][C:15](=[O:19])[C:16](O)=[O:17].[Cl-].[NH4+]>C1COCC1.[Cl-].[Zn+2].[Cl-]>[CH3:11][O:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:16](=[O:17])[C:15]([O:14][CH3:13])=[O:19]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 129271621-Bromo-2-(methoxymethyl)benzeneHCID 86640482Oxalic acid monomethyl ester chloride

생성물 1

HCID 19937173Methyl 2-methoxymethylphenylglyoxylate수율 57.7%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
20 °C

실험 절차

500 ml of an ethereal 1 M zinc chloride solution was dripped into a Grignard solution prepared from 12.0 g (0.46 mol) of magnesium shavings and 99.5 g (0.5 mol) of 1-bromo-2-methoxymethylbenzene in 500 ml of THF. The mixture was then refluxed for 1 hour, and a solution of 61.2 g (0.5 mol) of oxalic acid methyl ester chloride in 100 ml of THF was dripped in at an internal temperature of (-10)° C. After the mixture had been heated to about 20° C. it was stirred for a further 20 hours and then hydrolyzed with saturated ammonium chloride solution. After extraction with ether the combined ether phases were washed with water, dried and evaporated down. There was obtained 60 g of product (57.7%) as a mobile liquid.

후처리

  1. temperatureThe mixture was then refluxed for 1 hour
  2. extractionAfter extraction with ether the combined ether phases
  3. washwere washed with water
  4. customdried
  5. customevaporated down

출처 및 근거

ORD 기록
ord-5953b0e084ff4fe593745937720da0a3
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416068

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