Formaldehyde → Methylene bis(chloroacetate)

HRID 580806Notes

Reaction equation

HRID 580806 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-6e438629195d42f1b427efcc36b88f9d
Source dataset
uspto-grants-1999_07
Patent number
US05919753

Reaction notes

Loading…