Ammonium Chloride → Methyl 2-methoxymethylphenylglyoxylate

HRID 36603

Reaction equation

HRID 36603 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 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.

Workup

  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

Sources & evidence

ORD record
ord-5953b0e084ff4fe593745937720da0a3
Source dataset
uspto-grants-1995_05
Patent number
US05416068

Linked notes

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