Hydrochloric Acid → Ethyl 2-(2-methoxyphenyl)acetoacetate

HRID 1003155Notes

Reaction equation

HRID 1003155 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH3:15][C:16](C)([O-:18])C.[Na+].C(OCC)(=O)C.Cl>C(OC(C)C)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([C:16]([CH3:15])=[O:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 80160Ethyl (2-methoxyphenyl)acetateHCID 23676156Sodium t-butoxide

Product 1

HCID 22118306Ethyl 2-(2-methoxyphenyl)acetoacetateYield 60.2%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 2-methoxyphenyiacetate (11.6 g), sodium tert-butoxide (12.7 g) and ethyl acetate (15.8 g) in diisopropylether was heated at 70° C. for 2.5 hours and stirred at room temperature overnight. Ethyl acetate and hydrochloric acid (2M) were added and the organic phase dried (magnesium sulphate) and evaporated. The residue was distilled in vacuo to give ethyl 2-(2-methoxyphenyl)acetoacetate as a liquid (8.5 g), NMR 1.15 and 1.13(t,3h), 1.8 and 2.2(s,3H), 3.75 and 3.85(s,3H), 4.1-4.3(2q,2H), 5.15(s,1H), 6.9-7.3(m,4H), 13.1(s,1H).

Workup

  1. dry with materialthe organic phase dried (magnesium sulphate)
  2. customevaporated
  3. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-2c4291d4e9fe4beb95a2cc965c33b5fb
Source dataset
uspto-grants-2000_04
Patent number
US06046135

Reaction notes

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