Hydrochloric Acid → 1-phenylbut-3-yn-1-ol

HRID 259988Notes

Reaction equation

Cl[C:2](=[CH2:12])[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[OH-].[Na+].Cl>CN(C)C=O>[C:6]1([CH:4]([CH2:3][C:2]#[CH:12])[OH:5])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

40.00 Grams of the 2-chloroallylphenylcarbinol obtained above were dissolved in 400 g of N,N-dimethylformamide, and 17.52 g of sodium hydroxide in a flake form were added. The mixture was stirred at 25° C. for 7 hours. After the reaction was completed, the reaction mixture was neutralized with concentrated hydrochloric acid, and insolubles were filtered off. The filtrate was concentrated under reduced pressure, and then the concentration residue was subjected to extraction with toluene, washed with a 7% sodium carbonate aqueous solution and dried over sodium sulfate. The desiccant was filtered off, and the toluene was distilled off under reduced pressure. The resultant oily substance was distilled under reduced pressure to give 30.84 g of phenylpropargylcarbinol. The results were as follows.

Workup

filtrationwere filtered off
concentrationThe filtrate was concentrated under reduced pressure
extractionthe concentration residue was subjected to extraction with toluene
washwashed with a 7% sodium carbonate aqueous solution
dry with materialdried over sodium sulfate
filtrationThe desiccant was filtered off
distillationthe toluene was distilled off under reduced pressure
distillationThe resultant oily substance was distilled under reduced pressure

Sources & evidence

ORD record: ord-9a80ea45d6e147dcb5cbac053b8e0ee2
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523495

Reaction notes

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