Toluene → 1-Butanol, 3,3-dimethyl-2-[(phenylmethoxy)methyl]-

HRID 346253Notes

Reaction equation

HRID 346253 reaction equation
[C:1]([CH:5]([CH2:8][OH:9])[CH2:6][OH:7])([CH3:4])([CH3:3])[CH3:2].[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:16]([O:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:8][OH:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 1002262-Tert-butylpropane-1,3-diol

Product 1

HCID 106566691-Butanol, 3,3-dimethyl-2-[(phenylmethoxy)methyl]-

Conditions

Temperature
120 °C

Procedure

A mixture of 2-t-butylpropane-1,3-diol (11.0 g.) (E.L. Eliel et al J. Amer Chem Soc. 1968, 90, 3444) was stirred in dry toluene (200 ml), at 20° C. Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane, was added carefully to the stirred mixture. The mixture was stirred at 120° C. for 30 minutes and cooled. Benzyl bromide (9.5 ml) was added dropwise and the mixture heated at 130°, with stirring for 6 hours. The mixture was cooled, water was added and the mixture extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:4 diethyl ether: hexane. 2-Benzyloxymethyl-3,3-dimethyl-butan-1-ol (8.0 g) was obtained as a colourless

Workup

  1. washSodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane
  2. additionwas added carefully to the stirred mixture
  3. temperaturecooled
  4. additionBenzyl bromide (9.5 ml) was added dropwise
  5. temperaturethe mixture heated at 130°
  6. stirringwith stirring for 6 hours
  7. temperatureThe mixture was cooled
  8. additionwater was added
  9. extractionthe mixture extracted with diethyl ether
  10. washThe ethereal extracts were washed with water
  11. dry with materialdried over anhydrous magnesium sulphate
  12. customevaporated in vacuo
  13. customThe residue was purified by chromatography on silica
  14. washeluting with 1:4 diethyl ether

Sources & evidence

ORD record
ord-6c2a2413e0904fbbb8616dbd08cc8242
Source dataset
uspto-grants-1991_10
Patent number
US05061726

Reaction notes

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