Toluene → 2,6-Dimethyl-4-heptanol

HRID 1636960Notes

Reaction equation

HRID 1636960 reaction equation
[CH:1]1N=CN(C(N2C=NC=C2)=O)C=1.[OH-].[K+].C([C:17]([CH2:22][OH:23])(CO)[CH2:18][CH3:19])O.[C:24]1([CH3:30])[CH:29]=CC=C[CH:25]=1>>[CH3:25][CH:24]([CH2:30][CH:22]([OH:23])[CH2:17][CH:18]([CH3:19])[CH3:1])[CH3:29]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6510TrimethylolpropaneHCID 14797Potassium HydroxideHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 79572,6-Dimethyl-4-heptanol

Conditions

Temperature
55 °C

Procedure

CDI (0.55 g, 3.4 mmol) and KOH (0.1 g, 1.8 mmol) were added to a solution of CIH-HEAP-HEAP-OH (4 g, 3.33 mmol) (as prepared in Example 2(b)) in toluene 50 ml. The reaction mixture was heated to 50-60° C. under nitrogen or 5 hours. Trimethylolpropane (0.15 g, 1.11 mmol) was added and the mixture was stirred for a further 3 hours. The reaction mixture was allowed to cool overnight. The crystallised solid was removed by filtration and the filtrate concentrated in vacuo. The residue was dissolved in dichloromethane, washed with water, dried (MgSO4), filtered and concentrated in vacuo to give the dendrimer product (CIH-HEAP-HEAP-TMP) shown below as a clear viscous liquid (3.96 g, 92%) ##STR54##

Workup

  1. temperatureto cool overnight
  2. customThe crystallised solid was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17134364a7fc42d897f7204cf79e6830
Source dataset
uspto-grants-2000_03
Patent number
US06037444

Reaction notes

Loading…