Ammonia → 4-Ethynylphenol

HRID 365976Notes

Reaction equation

HRID 365976 reaction equation
OC#CC1C=CC=CC=1.[CH3:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.N.[Na].[Cl-].[NH4+]>O>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]#[CH:10])=[CH:14][CH:15]=1

Participants

8

Reactant 6

HCID 222AmmoniaHCID 74694'-HydroxyacetophenoneHCID 24819Phosphorus pentachlorideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 10909551Hydroxyphenylacetylene

Product 1

HCID 327584-EthynylphenolYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The conventional preparation process of hydroxyphenyl-acetylene has been reported, for example, in Izv. Akad. Nauk SSSR Se. r. Khim 1964(11), 2073-4. In the process, 4-hydroxyacetophenone is chlorinated with phosphorus pentachloride, reacted in liquid ammonia in the presence of metallic sodium and ammonium chloride, and successively treated with water to obtain 4-hydroxyphenylacetylene in 46% yield.

Sources & evidence

ORD record
ord-d67d156f7ed84820974bbda2360448e5
Source dataset
uspto-grants-2000_10
Patent number
US06127583

Reaction notes

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