Hydrochloric Acid → 2-Hydroxymethyl-4-methoxymethyl-1,5-diisopropylbenzene

HRID 846880Notes

Reaction equation

HRID 846880 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[C:6]([CH:11]([CH3:13])[CH3:12])=[CH:5][C:4]=1[CH:14]([CH3:16])[CH3:15].[CH3:17]I.[H-].[Na+].Cl>O1CCCC1>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:17])[C:6]([CH:11]([CH3:12])[CH3:13])=[CH:5][C:4]=1[CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14850545(4,6-Diisopropyl-1,3-phenylene)dimethanol

Product 1

HCID 148505462-Hydroxymethyl-4-methoxymethyl-1,5-diisopropylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

31.5 g (0.14 mol) of the compound from Example 3 and 9.6 ml (0.15 mol) of methyl iodide are added under a nitrogen atmosphere to 8.9 g (0.3 mol) of sodium hydride (80% strength in paraffin oil) in 500 ml of tetrahydrofuran. After stirring for 2 h at 80° C., the mixture is cautiously hydrolyzed using 30 ml of dilute hydrochloric acid, the solvent is distilled off, and the residue is taken up in methylene chloride, washed with water, dried and chromatographed on silica gel (230-400 mesh, ethyl acetate/petroleum ether 1:2).

Workup

  1. distillationthe solvent is distilled off
  2. washwashed with water
  3. customdried
  4. customchromatographed on silica gel (230-400 mesh, ethyl acetate/petroleum ether 1:2)

Sources & evidence

ORD record
ord-8b7e1630f5c84bc9a32cc8f65f985ec8
Source dataset
uspto-grants-1992_08
Patent number
US05138090

Reaction notes

Loading…