Water → HCID 67345954, compound

HRID 1669363Notes

Reaction equation

HRID 1669363 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[CH3:10][O:11][C:12](=[O:16])[C:13](Cl)=[O:14].O>O1CCCC1>[CH3:10][O:11][C:12]([C:13]([NH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6])=[O:14])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 79846Methyl chloroglyoxylateHCID 802933-Aminobenzyl alcohol

Product 1

HCID 67345954HCID 67345954, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4.93 g of m-aminobenzyl alcohol in 50 ml of tetrahydrofuran was added dropwise a solution of 3.7 ml of chloroglyoxylic acid methyl ester in 20 ml of tetrahydrofuran, and this was stirred at room temperature for 1.5 hours. To the reaction solution was added water, and this was extracted with ethyl acetate, and washed with an aqueous saturated sodium chloride solution. After dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 5.10 g of 3-[(methoxycarbonyl)carbonylamino]benzyl alcohol as a white solid.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialAfter dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-abb840f631984afbb4f0f462713e20b3
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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