Dimethylformamide → HCID 86661490, compound

HRID 1626741Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[C:12]1([C:18]2[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(OCC)(=O)C.O>[C:12]1([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[O:24][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.34 g (9.72 mmol) of potassium carbonate was added to a DMF (10 mL) solution comprising 564 mg (3.24 mmol) of 3-(cyclohex-1-en-1-yl)phenol and 541 mg (3.82 mmol) of ethyl bromoacetate. The mixture was heated while stirring at 80° C. for 3 hours, and then cooled to room temperature. Water and ethyl acetate were added thereto, and extraction was performed. The organic layer was then separated, washed with water 3 times, and washed with saturated saline once. The organic layer was dried over sodium sulfate, and filtered. Thereafter, the filtrate was condensed, followed by drying under reduced pressure, thereby giving 777 mg of ethyl [3-(cyclohex-1-en-1-yl)phenoxy]acetate (yield: 92%).

Workup

temperatureThe mixture was heated
temperaturecooled to room temperature
extractionextraction
customThe organic layer was then separated
washwashed with water 3 times
washwashed with saturated saline once
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customcondensed
customby drying under reduced pressure

Sources & evidence

ORD record: ord-8642b4f3a1ec448c920af9652477cc6a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785473B2

Reaction notes

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