Chloroacetic Acid → Methyl 2-(propan-2-yloxy)acetate

HRID 2233147Notes

Reaction equation

HRID 2233147 reaction equation
[Na].Cl[CH2:3][C:4]([OH:6])=[O:5].[CH3:7][CH:8]([CH3:10])[O-:9].[Na+].[CH:12](O)(C)C>O>[CH:8]([O:9][CH2:3][C:4]([O:6][CH3:12])=[O:5])([CH3:10])[CH3:7]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 3776IsopropanolHCID 5360545Sodium2×HCID 109204432-Propanol, sodium salt (1:1)

Product 1

HCID 23192059Methyl 2-(propan-2-yloxy)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

116.5 g of the sodium salt of chloracetic acid are slowly added at 80° C. to a sodium isopropoxide solution (freshly prepared from 23 g of sodium and 250 ml of isopropylalcohol). The reaction mixture is refluxed for 2 hours and then combined with 500 ml of water. The mixture is evaporated down to a total volume of 200 ml and adjusted to pH1 with conc. sulphuric acid. The precipitate formed is filtered off, the two phases of the filtrate are and the organic phase is fractionally distilled in vacuo (101-103° C./10 Torr; 83 g; 70%). The 2-isopropoxy-acetic acid thus obtained is heated together with 0.2 ml of conc. sulphuric acid in 57 ml of methanol and 200 ml benzene for 7 hours using a water separator. After the excess methanol has been distilled off the residue is fractionally distilled in vacuo (50-55° C./10 Torr; 81.6 g; 88%).

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. customThe mixture is evaporated down to a total volume of 200 ml
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. distillationthe organic phase is fractionally distilled in vacuo (101-103° C./10 Torr; 83 g; 70%)

Sources & evidence

ORD record
ord-11b29b4b29724e4ab9b4fe82b8366d78
Source dataset
uspto-grants-2010_05
Patent number
US07709480B2

Reaction notes

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