Propargyl alcohol → p-[(1,5-Dimethylhexyl)oxy]benzoic acid propargyl ester

HRID 1390401Notes

Reaction equation

HRID 1390401 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:6][CH:5]=1.C[O-].[Na+].[CH2:23](O)[C:24]#C>>[CH2:1]([O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])=[CH:6][CH:5]=1)[C:23]#[CH:24]

Participants

4

Reactant 3

HCID 7859Propargyl alcohol2×HCID 10942334Sodium MethoxideHCID 54404637HCID 54404637, compound

Product 1

HCID 53978508p-[(1,5-Dimethylhexyl)oxy]benzoic acid propargyl ester

Procedure

10 g of p-[(1,5-dimethylhexyl)oxy]benzoic acid methyl ester, 30 ml of propargyl alcohol and 0.5 g of sodium methoxide are heated to reflux for 1/2 an hour. The excess propargyl alcohol is thereupon slowly (5 hrs.) distilled off. The residue is poured onto water and extracted with diethyl ether. The ether solution is dried with sodium sulfate and evaporated. The dark-yellow p-[(1,5-dimethylhexyl)oxy]benzoic acid propargyl ester obtained is purified over kieselgel.

Workup

  1. temperatureto reflux for 1/2 an hour
  2. distillationslowly (5 hrs.) distilled off
  3. additionThe residue is poured onto water
  4. extractionextracted with diethyl ether
  5. dry with materialThe ether solution is dried with sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-8b613164ea15411cabfec3ddfdeefa36
Source dataset
uspto-grants-1979_02
Patent number
US04138579

Reaction notes

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