Acetyl chloride → 3-[4-(4-Chlorophenoxy)phenyl]-3-hydroxybut-1-yne

HRID 1764171Notes

Reaction equation

HRID 1764171 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[C:15](Cl)(=O)C.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:23]1C[O:26][CH2:25][CH2:24]1>CS(C)=O>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][C:4]2[CH:3]=[CH:2][C:1]([C:25]([OH:26])([CH3:15])[C:24]#[CH:23])=[CH:6][CH:5]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran2×HCID 234364-Chlorophenyl phenyl etherHCID 6451240Aluminum(III) Chloride

Product 1

HCID 203455993-[4-(4-Chlorophenoxy)phenyl]-3-hydroxybut-1-yne

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2.47 g. of 4'-chloro-4-acetyldiphenyl ether, which can be prepared from 4-chlorodiphenyl ether and acetyl chloride in the presence of AlCl3, in 6 ml. of THF and 2 ml. of DMSO is added dropwise to a suspension of 1.38 g. of lithium acetylide/ethylenediamine complex in a mixture of 3 ml. of absolute THF and 4 ml. of absolute DMSO, while acetylene is bubbled through the mixture. The mixture is stirred for one hour while under nitrogen blanketing. An aqueous solution of ammonium chloride is added to the solution, which contains lithium 3-[4-(4-chlorophenoxy)phenyl]-but-1-yn-3-olate and the mixture is poured into water and worked up in the customary manner to give 3-[4-(4-chlorophenoxy)phenyl]-3-hydroxybut-1-yne, m.p. 55°-57°.

Workup

  1. additionof lithium acetylide/ethylenediamine complex in a mixture of 3 ml
  2. customof absolute DMSO, while acetylene is bubbled through the mixture
  3. additionAn aqueous solution of ammonium chloride is added to the solution, which
  4. additionthe mixture is poured into water

Sources & evidence

ORD record
ord-55bd1118a6504a99a0307940efb2f28d
Source dataset
uspto-grants-1978_09
Patent number
US04115456

Reaction notes

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