Hydrochloric Acid → HCID 15734662, compound

HRID 1508181Notes

Reaction equation

HRID 1508181 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].[CH2:14]=O.C[O-].[Na+].Cl>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=[CH2:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 2734106Methyl 2,4-dichlorobenzeneacetateHCID 10942334Sodium Methoxide

Product 1

HCID 15734662HCID 15734662, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,4-dichlorophenylacetic acid methyl ester (4.62 mmol) in 9 mL DMSO were added paraformaldehyde (4.85 mmol) and NaOMe (0.23 mmol). The reaction mixture was stirred at RT for 1 h and then poured into ice cold water. The mixture was neutralized with 1M HCl solution and extracted with toluol (3×). The combined organic layers were washed with aq. NaCl solution, dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (9/1 to 8/2) gives the desired compound as colorless oil;

Workup

  1. additionpoured into ice cold water
  2. extractionextracted with toluol (3×)
  3. washThe combined organic layers were washed with aq. NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-551af1866bc84f83891b7354eef75cca
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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