Ethyl Acetoacetate → HCID 53744655, compound

HRID 2072226Notes

Reaction equation

HRID 2072226 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19](=[O:24])[CH2:20][C:21]([CH3:23])=[O:22])[CH3:17].[NH4+].[Cl-]>CCOCC>[CH2:16]([O:18][C:19](=[O:24])[CH2:20][C:21]([C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)([OH:22])[CH3:23])[CH3:17]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 25517Ammonium ChlorideHCID 178419636HCID 178419636, compound

Product 1

HCID 53744655HCID 53744655, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of p-phenoxyphenylmagnesium bromide (obtained from 2.49 g. of 4-bromodiphenyl ether and 0.24 g. of magnesium in 100 ml. of ether) is added dropwise at 20°, with stirring, to a solution of 1.3 g. of acetoacetic acid ethyl ester in 40 ml. of ether, and the mixture is stirred for a further two hours, the resulting alcoholate is decomposed by means of ice and saturated NH4Cl solution, and the ethereal phase is dried and evaporated to give 3-p-phenoxyphenyl-3-hydroxybutyric acid ethyl ester.

Workup

  1. customthe ethereal phase is dried
  2. customevaporated

Sources & evidence

ORD record
ord-8214920da2ff4daaafe92c12701ec5b4
Source dataset
uspto-grants-1977_09
Patent number
US04049823

Reaction notes

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