Ammonium Chloride → Methyl 2-methoxymethylphenylglyoxylate

HRID 488019

Reaction equation

HRID 488019 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 19937173Methyl 2-methoxymethylphenylglyoxylateYield 57.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2dc1ba16547544328f2c8be48f369ed1
Source dataset
uspto-grants-1994_03
Patent number
US05298527

Linked notes

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