Isopropyl iodide → 3-Ethoxy-4-isopropoxybenzaldehyde

HRID 1438183Notes

Reaction equation

HRID 1438183 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH:20]([CH3:22])[CH3:21]>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH:20]([CH3:22])[CH3:21])[CH:7]=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 8467EthylvanillinHCID 11430Potassium Carbonate

Product 1

HCID 8747303-Ethoxy-4-isopropoxybenzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To 3-ethoxy-4-hydroxybenzaldehyde (20.0 g, 120 mmol) in dimethylformamide (250 mL) was added potassium carbonate (33.1 g, 240 mmol) then 2-iodopropane (18 mL, 180 mmol). The reaction mixture was heated to 45° C. and stirred for 3 h. After cooling to rt, the crude reaction mixture was extracted with ethyl acetate (3×). The combined extracts were then washed with water (3×) then brine and dried over sodium sulfate. The solvent was removed to give 24 g of 141A as a yellow oil. LC-MS: 231.17 (M+Na)+.

Workup

  1. temperatureAfter cooling to rt
  2. customthe crude reaction mixture
  3. extractionwas extracted with ethyl acetate (3×)
  4. washThe combined extracts were then washed with water (3×)
  5. dry with materialbrine and dried over sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-7024f68d15474dd3b07bf62a494df3a7
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

Loading…