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

HRID 1390402Notes

Reaction equation

HRID 1390402 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.[CH2:20](O)[C:21]#C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[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:20]#[CH:21]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7859Propargyl alcohol2×HCID 54404637HCID 54404637, compound

Product 1

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

Procedure

13 g of p-[(1,5-dimethylhexyl)oxy]benzoic acid methyl ester is heated to reflux with 9 g of propargyl alcohol and 0.1 g of p-toluenesulphonic acid. The excess propargyl alcohol is thereupon slowly (5 hrs.) distilled off. The residue is poured onto water and extracted with diethyl ether. The ether phase is dried with sodium sulfate and evaporated. There is obtained dark-yellow p-[(1,5-dimethylhexyl)oxy]benzoic acid propargyl ester which is purified on Kieselgel.

Workup

  1. distillationslowly (5 hrs.) distilled off
  2. additionThe residue is poured onto water
  3. extractionextracted with diethyl ether
  4. dry with materialThe ether phase is dried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-7e44eb09f9e54fe7ab797be45c72927f
Source dataset
uspto-grants-1979_02
Patent number
US04138579

Reaction notes

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