p-Toluenesulfonic acid → HCID 20206179, compound

HRID 2166552Notes

Reaction equation

HRID 2166552 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[OH:17])([CH3:9])[CH3:8].[CH2:19](O)[CH2:20][CH2:21][CH2:22][CH2:23]C.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[OH:17])([CH3:9])[CH3:8])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 81031-HexanolHCID 20206153HCID 20206153, compound

Product 1

HCID 20206179HCID 20206179, compound

Procedure

5.5 parts of methyl-5-(2,4-dihydroxyphenyl)-5-methylhexanoate, 50 parts of n-hexanol, and 0.5 parts of p-toluene sulphonic acid are heated on a steam-bath for 6 hours. The excess hexanol is then removed under reduced pressure and then residual oil taken up in ether, washed with sodium bicarbonate solution, water, and evaporated. Short path distillation of the residual oil at a pressure of 0.5 mm of mercury yields 5.8 parts of n-hexyl-5-(2,4-dihydroxyphenyl)-5-methylhexanoate of the formula ##STR19## with the following percentage composition by weight:

Workup

  1. customThe excess hexanol is then removed under reduced pressure
  2. washwashed with sodium bicarbonate solution, water
  3. customevaporated
  4. distillationShort path distillation of the residual oil at a pressure of 0.5 mm of mercury

Sources & evidence

ORD record
ord-8d12ec64867b458ea9fb2eeaea12b167
Source dataset
uspto-grants-1983_06
Patent number
US04387158

Reaction notes

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