Formaldehyde → HCID 71239437, compound

HRID 1508180Notes

Reaction equation

HRID 1508180 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12].C=O.[C:16]([O-])(O)=[O:17].[Na+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 2734106Methyl 2,4-dichlorobenzeneacetate

Product 1

HCID 71239437HCID 71239437, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 2,4-dichlorophenylacetic acid methyl ester (1.38 mmol) and paraformaldehyde (1.45 mmol) in 2.7 mL DMSO was added NaHCO3 (0.07 mmol). The reaction mixture was stirred at RT for 2 h and then quenched with water. The mixture was neutralized with 1M HCl solution and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept to Hept/EtOAc (1/1) gives the desired compound as colorless oil;

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-6a28941b89244a69b463fbd8967008db
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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