Diethyl Ether → Methyl 4(4-iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetate

HRID 133680Notes

Reaction equation

HRID 133680 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[CH3:19]COCC>CC(O)=O>[I:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([O:16][CH3:19])=[O:15])=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 113143824-(4Iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetic acid

Product 1

HCID 15380042Methyl 4(4-iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetateYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a solution of 12.6 g of 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetic acid, prepared in accordance with Example 3, in 100 mL of Et2O cooled in an ice bath, was added 40 mL of ethereal CH2N2. The mixture was stirred at 0 C for few minutes, then let stand for 2 hr. A few drops of AcOH were added to decompose excess CH2N2, then the mixture was filtered and stripped to afford 12.6 g (96%) of methyl 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetate.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-c850e9657cba4c8b928868e9308c93a2
Source dataset
uspto-grants-2008_06
Patent number
US07390906B2

Reaction notes

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