Methyl Ethyl Ketone → Phenylmethoxy-2,4-hexandione

HRID 274596Notes

Reaction equation

HRID 274596 reaction equation
[CH3:1][C:2](=[O:5])[CH2:3][CH3:4].[NH2-].[Na+].[C:8]1([CH2:14][O:15][CH2:16][C:17]([O:19]C)=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[C:8]1([CH2:14][O:15][CH2:16][C:17](=[O:19])[CH2:1][C:2](=[O:5])[CH2:3][CH3:4])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 24533Sodium amideHCID 11745225Methyl 2-(benzyloxy)acetate

Product 1

HCID 20093386Phenylmethoxy-2,4-hexandione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-Butanone (47.65 ml) was added dropwise over 10 min to a mechanically stirred suspension of sodium amide (95%; 20.78 g) dry ether (600 ml) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 15 min. A solution of methyl phenylmethoxyacetate (48.0 g) in dry ether (50 ml) was added dropwise over 13 min at room temperature under nitrogen, and the reaction progressed according to the method of Intermediate 16, to give the title compound as a yellow oil (23.35 g)

Sources & evidence

ORD record
ord-c45f57fa98ec4e148360d6c29366760f
Source dataset
uspto-grants-1995_02
Patent number
US05389659

Reaction notes

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