Ethanol → (2-Isopropoxyphenyl)methanol

HRID 899078Notes

Reaction equation

HRID 899078 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[C:10]([O-])([O-])=O.[K+].[K+].[CH2:16](O)[CH3:17]>>[CH:16]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])([CH3:17])[CH3:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 5146Salicyl AlcoholHCID 11430Potassium Carbonate

Product 1

HCID 12071269(2-Isopropoxyphenyl)methanolYield 99%

Procedure

A mixture of 2-hydroxybenzyl alcohol (21.04 g, 1 equiv., available from Aldrich Chemical Company), 2-isopropyl iodide (32.3 mL, 1.9 equiv., available from Aldrich Chemical Company) and K2CO3 (71.42 g, 3 equiv.) in ethanol was refluxed for 3 hours. On cooling the reaction mixture was filtered and the solvent removed under reduced pressure and replaced with dichloromethane, and then filtered and the solvent removed to give the title compound as an oil (27.751 g, 99%). 1H NMR (300 MHz, CDCl3): δ 1.37 (d, 6H, J=6.0 Hz), 3.55 (bs, 1H), 4.50-4.70 (m, 3H), 6.78-6.90 (m, 2H), 7.15-7.25 (m, 2H).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureOn cooling the reaction mixture
  3. filtrationwas filtered
  4. customthe solvent removed under reduced pressure
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-cd24e2bef9cc4c3dbc3e8be6afa276e5
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

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