Isooctan-1-ol → HCID 18672828, compound

HRID 1058108Notes

Reaction equation

HRID 1058108 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]2=[N:7][N:8]([C:10]3[CH:11]=[C:12]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=3[OH:21])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[N:9]=[C:5]2[CH:4]=1.[CH2:30](O)[CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:29][C:2]([C:3]1[C:4]2[C:5](=[N:9][N:8]([C:10]3[CH:11]=[C:12]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=3[OH:21])[CH2:13][CH2:14][C:15]([O:17][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:16])[N:7]=2)[CH:6]=[CH:26][CH:27]=1)([F:28])[F:1]

Participants

4

Reactant 3

HCID 15450Isooctan-1-olHCID 521998p-Toluenesulfonic acid monohydrateHCID 18674751HCID 18674751, compound

Product 1

HCID 18672828HCID 18672828, compoundYield 99.5%

Procedure

The acid prepared in Example 39 (8 g, 0.02 mol), EXXAL® 8 (isooctanol isomers, Exxon, 5 g, 0.038 mol), p-toluenesulfonic acid hydrate (0.5 g, 0.0026 mol) and xylenes (100 mL) are charged to a reactor and refluxed for six hours. TLC shows when the reaction is complete. The solvent is removed and the resulting oil is chromatographed on silical gel. The title compound is obtained in 99.5% yield as a light yellow oil.

Workup

  1. temperaturerefluxed for six hours
  2. customThe solvent is removed
  3. customthe resulting oil is chromatographed on silical gel

Sources & evidence

ORD record
ord-5657846f928344a1836d4943f0c43ba2
Source dataset
uspto-grants-2003_02
Patent number
US06515051B2

Reaction notes

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