Hydrochloric Acid → Methyl 2,2-dimethylacetoacetate

HRID 1248811Notes

Reaction equation

HRID 1248811 reaction equation
[CH3:1][CH2:2][O:3]CC.Br[C:7]([CH3:13])([CH3:12])[C:8]([O:10][CH3:11])=[O:9].C(OC(=O)C)(=O)C.Cl>[Zn].C1C=CC=CC=1>[CH3:12][C:7]([CH3:13])([C:2](=[O:3])[CH3:1])[C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 90097Methyl 2-bromo-2-methylpropionate

Product 1

HCID 96925Methyl 2,2-dimethylacetoacetate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

To a mixture of 20.86 g of 20 mesh zinc metal, 165 ml of 120:210 by volumes ether:benzene and 0.05 g of mercuric chloride was added a few drops of a solution of 26.64 g of methyl alpha-bromoisobutyrate and 18.72 g of acetic anhydride followed by brief heating with a heat gun to initiate the reaction. The remaining solution was added slowly at reflux. After addition was complete, the mixture was refluxed for 21/2 hrs, cooled, poured over 12 ml concentrated HCl mixed with ice, and extracted with ether. The combined extract was washed with water, dried (MgSO4) and stripped to give 23.15 g of a yellow oil. Distillation yielded 15.41 g of the desired product as a colorless oil, b.p. 32° C. (1 mm Hg).

Workup

  1. temperatureby brief heating with a heat gun
  2. customthe reaction
  3. additionThe remaining solution was added slowly
  4. temperatureat reflux
  5. additionAfter addition
  6. temperaturethe mixture was refluxed for 21/2 hrs
  7. temperaturecooled
  8. additionmixed with ice
  9. extractionextracted with ether
  10. extractionThe combined extract
  11. washwas washed with water
  12. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-be5333c7642e47edb1a4048df1fa396d
Source dataset
uspto-grants-1986_12
Patent number
US04626543

Reaction notes

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