Pyridine → Diprop-2-yn-1-yl benzene-1,4-dicarboxylate

HRID 2398312Notes

Reaction equation

HRID 2398312 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:13]([OH:16])[C:14]#[CH:15].CC[O:19][CH2:20][CH3:21].N1C=CC=C[CH:23]=1>O>[CH2:13]([O:16][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:19][CH2:20][C:21]#[CH:23])=[O:7])=[CH:4][CH:3]=1)[C:14]#[CH:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7488Terephthaloyl chlorideHCID 7859Propargyl alcohol

Product 1

HCID 352136Diprop-2-yn-1-yl benzene-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 10.15 g. of terephthaloyl chloride, 8.41 g. propargyl alcohol and 200 ml. anhydrous ether at 5° under nitrogen is slowly added with stirring 16.1 ml. of pyridine. The reaction mixture is stirred for 4 hours at 5° and for 21/2 hour at room temperature. Water (2 ml.) is added and the mixture is stirred for 1/2 hour. Additional water (100 ml.) is added, the organic layer is extracted with ether and pentane and the reaction mixture is worked up using the procedure of Example 1 to yield bis(propargyl)terephthalate, m.p. 109-109.5.

Workup

  1. additionTo a mixture of 10.15 g
  2. stirringThe reaction mixture is stirred for 4 hours at 5° and for 21/2 hour at room temperature
  3. stirringthe mixture is stirred for 1/2 hour
  4. extractionthe organic layer is extracted with ether and pentane

Sources & evidence

ORD record
ord-af22b60316df4255a88e02e15ab8bac9
Source dataset
uspto-grants-1977_05
Patent number
US04024278

Reaction notes

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