Potassium Carbonate → 2-(Tert-butoxy)acetic acid

HRID 4371

Reaction equation

HRID 4371 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][CH2:12][C:13]([O:15]CCCC)=[O:14])([CH3:10])([CH3:9])[CH3:8]>CO.O>[C:7]([O:11][CH2:12][C:13]([OH:15])=[O:14])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14050415Butyl tert-butoxyacetate

Product 1

HCID 27609982-(Tert-butoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To 100 ml of a 50:50 (v/v) methanol/water solution containing 14.35 g of potassium carbonate, was added n-butyl 2-tert-butoxyacetate (6.50 g, 0.0346 mol). The mixture was heated at reflux for 17 hours and the volatiles removed on a flash evaporator. The remaining solution was cooled to approximately 0° C. and acidified to pH 3-4 with cold 50% aqueous hydrogen chloride. The product was extracted with ether, the ether extract washed with brine and dried over magnesium sulfate, then concentrated in vacuo to give the title compound as a yellow liquid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 17 hours
  3. customthe volatiles removed on a flash evaporator
  4. extractionThe product was extracted with ether
  5. extractionthe ether extract
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-683c16909174462faf1b49adbea715f3
Source dataset
uspto-grants-1988_02
Patent number
US04725620

Linked notes

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