p-Toluenesulfonic acid monohydrate → tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one

HRID 703683Notes

Reaction equation

HRID 703683 reaction equation
[CH2:1]([C@H:7]([CH:11]([OH:32])[CH2:12][CH:13](OC1CCCCO1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:8](O)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH2:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([C@@H:7]1[CH:11]([OH:32])[CH2:12][CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:33][C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 678557542-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid

Product 1

HCID 67855756tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.4 g of a diastereomer mixture of 2-hexyl-3-hydroxy-(R)-5 [(tetrahydro-2H -pyran-2-yl)oxy]hexadecanoic acid are dissolved in 160 ml of ethanol and 800 mg of toluene-4-sulphonic acid monohydrate are added. The reaction mixture is heated to 55°-60° C. until the reaction has finished. The solvent is removed in vacuo and the residue is dissolved in 160 ml of dichloromethane. The solution is stirred at room temperature for 1 hour. The reaction mixture is evaporated. The material obtained is chromatographed on silica gel. There is obtained tetrahydro-3-hexyl-4-hydroxy-(R)-6-undecyl-2H-pyran-2-one, m.p. 95°-96° C.

Workup

  1. temperatureThe reaction mixture is heated to 55°-60° C. until the reaction
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in 160 ml of dichloromethane
  4. customThe reaction mixture is evaporated
  5. customThe material obtained
  6. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-01d7d0a81f374c4f888157fbe69620a6
Source dataset
uspto-grants-1991_01
Patent number
US04983746

Reaction notes

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