Isooctan-1-ol → HCID 18672828, compound

HRID 990206Notes

Reaction equation

HRID 990206 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-bc179a9460c24eae9924f856274ef6fb
Source dataset
uspto-grants-2002_10
Patent number
US06458872B1

Reaction notes

Loading…