tert-Butanol → Tert-butyl 3-(3-iodophenyl)-3-oxopropanoate

HRID 1375684Notes

Reaction equation

HRID 1375684 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH2:9][C:10](OCC)=[O:11])[CH:5]=[CH:6][CH:7]=1.[C:16]([OH:20])([CH3:19])([CH3:18])[CH3:17]>>[I:1][C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH2:9][C:10]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 2759369Ethyl (3-iodobenzoyl)acetate

Product 1

HCID 69508156Tert-butyl 3-(3-iodophenyl)-3-oxopropanoateYield 38%

Procedure

Ethyl 3-(3-iodophenyl)-3-oxopropanoate (29.3 g, 92.1 mmol) was heated to 120° C. in a sealed tube in t-butanol (80 mL) for 4 hours. The mixture was concentrated in vacuo and purified by column chromatography (0–3% ethyl acetate in hexanes) to provide the titled compound (12.1 g, 38%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by column chromatography (0–3% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-96bea1d70b5246ef96a59b516ecb7738
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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