Ammonium Chloride → Methyl 2-methoxymethylphenylglyoxylate

HRID 488019

反応式

HRID 488019 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 19937173Methyl 2-methoxymethylphenylglyoxylate収率 57.7%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
20 °C

実験手順

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 hours, 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.

後処理

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

出典と根拠

ORDレコード
ord-2dc1ba16547544328f2c8be48f369ed1
出典データセット
uspto-grants-1994_03
特許番号
US05298527

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