Hydrochloric Acid → HCID 21583933, compound

HRID 330750Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:14]1([CH:20]([CH3:25])[CH2:21][C:22](Cl)=[O:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:14]1([CH:20]([CH3:25])[CH2:21][C:22]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To the solution of phenol (8.62 g, 92 mmol) and 4-dimethylaminopyridine (400 mg) in toluene (110 ml) was added pyridine (18.1 g, 229 mmol) and the resulting solution was cooled to 10° C. Then a solution of 3-phenylbutanoyl chloride (20.1 g, 110 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 24 h, and then cooled to 5° C. before the careful addition of 2N aq. HCl-solution (225 ml). The mixture was stirred intensely for 15 min, then diluted with toluene and transferred into a separatory funnel. The aqueous layer was separated and the organic layer washed 4 times with water, then brine and dried over MgSO4. The solvent was removed in a rotary evaporator and the residue short-path distilled at 125-128° C./0.07 mbar to yield 18.52 g (70%) of colourless oil.

Workup

stirringThe mixture was stirred intensely for 15 min
customtransferred into a separatory funnel
customThe aqueous layer was separated
washthe organic layer washed 4 times with water
dry with materialbrine and dried over MgSO4
customThe solvent was removed in a rotary evaporator
distillationthe residue short-path distilled at 125-128° C./0.07 mbar

Sources & evidence

ORD record: ord-65cf5a608b55415d88d1bb6eb4d45d64
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877704B2

Reaction notes

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