Potassium Carbonate → Tert-butyl (4-tert-butyl-3-chlorophenoxy)acetate

HRID 2108831

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[Cl:18])([CH3:10])([CH3:9])[CH3:8].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CC(C)=O>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:13][C:12]=1[Cl:18])([CH3:10])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of potassium carbonate (994 mg, 7.2 mmol) and 4-tert-butyl-3-chlorophenol (440 mg, 2.4 mmol) in acetone (5 ml) was added t-butyl bromoacetate (370 mg, 1.9 mmol) was added and the mixture was refluxed at 60° C. for 14 hours. Filtrating of potassium carbonate, evaporation, and purification through silica gel column chromatography eluting with hexane/EtOAc (20:1 to 10:1) to furnish the tert-butyl (4-tert-butyl-3-chlorophenoxy)acetate (720 mg, 100%). The mixture of tert-butyl (4-tert-butyl-3-chlorophenoxy)acetate (720 mg, 2.4 mmol), TFA (2.0 ml), DCM (2.0 ml) was stirred for 5 hours at room temperature. After being concentrated in vacuo, the residue was triturated with hexane to furnish the title compound (582 mg, 100%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 1.45 (9H, s), 4.67 (2H, s), 6.76 (1H, dd, J=2.6, 8.6 Hz), 6.96 (1H, d, J=2.6 Hz), 7.35 (1H, d, J=8.6 Hz).

Workup

additionwas added
filtrationFiltrating of potassium carbonate, evaporation, and purification through silica gel column chromatography
washeluting with hexane/EtOAc (20:1 to 10:1)

Sources & evidence

ORD record: ord-bbe265aa5f9f427889232584c30d740b
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514457B2

Linked notes

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