Formaldehyde → Methylene bis(chloroacetate)

HRID 260626

Reaction equation

HRID 260626 reaction equation
ClC[C:3]([O:5][C:6](=[O:9])[CH2:7][Cl:8])=[O:4].[CH2:10]=[O:11].[CH2:12]([Cl:14])Cl>S(=O)(=O)(O)O>[Cl:8][CH2:7][C:6]([O:5][CH2:3][O:4][C:10](=[O:11])[CH2:12][Cl:14])=[O:9]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 10946Chloroacetic anhydride

Product 1

HCID 86587291Methylene bis(chloroacetate)Yield 57%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Chloroacetic anhydride (12.75 g, 75 mmol), paraformaldehyde (2.25 g, 75 mmol) and conc. sulfuric acid (15 drops) are added to methylene chloride (15 ml). The mixture is stirred for 24 hrs. at 50° C. under nitrogen, whereafter the reaction mixture is extracted with saturated aqueous potassium carbonate until carbon dioxide emission ends. The organic layer is dried (MgSO4), evaporated to dryness and the residue is distilled (80° C., 0.15 mmHg) to yield 10.2 g (57%) product. 1H NMR (200 MHz, CDCl3): δ 4.1 (2×CH2Cl,s), 5.9 (CH2,s). 13C NMR (200 MHz, CDCl3): δ 41.1 (CH2Cl), 81.4 (O--CH2 --O), 166.4 (CO).

Workup

  1. extractionat 50° C. under nitrogen, whereafter the reaction mixture is extracted with saturated aqueous potassium carbonate until carbon dioxide emission
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customevaporated to dryness
  4. distillationthe residue is distilled (80° C., 0.15 mmHg)

Sources & evidence

ORD record
ord-f4dcb4ccdada4616975d8958bd41ed1b
Source dataset
uspto-grants-1996_06
Patent number
US05529766

Linked notes

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