Isopropyl iodide → HCID 19363071, compound

HRID 2425300Notes

Reaction equation

HRID 2425300 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].[OH-].[K+].I[CH:15]([CH3:17])[CH3:16]>C1COCC1.CC(OC)(C)C>[CH:15]([O:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([CH:6]=[O:7])=[CH:8][C:9]=1[CH3:10])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 19363071HCID 19363071, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-Hydroxy-3,5-dimethylbenzaldehyde (2.5 g, 16.6 mmol) in THF (100 mL) was treated with KOH (1.5 eq. of 1 N aq. solution, 25 mL) and 2-iodopropane (2.0 eq.) and heated at reflux for 5 days. The reaction was then cooled, transferred to a separatory funnel, diluted with MTBE, washed with H2O, 1 N NaOH (twice), 0.5 N HCl (aq.), brine, dried over MgSO4 and concentrated. The product was purified over silica gel on an ISCO combiflash to yield 1.99 g (10.34 mmol) 4-isopropoxy-3,5-dimethylbenzaldehyde as a colorless liquid. H1 NMR (300 MHz, CDCl3) 9.89 (s, 1H), 7.55 (s, 2H), 4.41-4.26 (m, 1H), 2.32 (s, 6H), 1.32 (d, J=6 Hz, 6H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 days
  3. temperatureThe reaction was then cooled
  4. customtransferred to a separatory funnel
  5. washwashed with H2O, 1 N NaOH (twice), 0.5 N HCl (aq.), brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe product was purified over silica gel on an ISCO combiflash

Sources & evidence

ORD record
ord-85b0294dc1ad43daa128e9c5cb2c3f20
Source dataset
uspto-grants-2011_06
Patent number
US07964624B1

Reaction notes

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