3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 991345Notes

Reaction equation

HRID 991345 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(O)(C)C>[CH:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 7129143-IsopropoxybenzaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

EX-645A) 3-Hydroxybenzaldehyde (5.60 g, 45.9 mmol) and 2-iodopropane (7.86 g, 46.2 mmol) were dissolved in 50 mL of isopropanol. Potassium carbonate (20 g, 145 mmol) was added, and the mixture was heated to reflux for 8 h, at which time TLC analysis indicated that the reaction had gone to completion. Water was added to dissolve all solids, and the mixture was extracted with ether (3x). The combined ether layer was washed with water, 2 M NaOH, again with water until clear (4x), and finally with brine. The solution was dried over MgSO4, filtered, and evaporated to give 5.03 g (67%) of the desired 3-isopropoxybenzaldehyde product as a pale oil. 1H NMR (C6D6) δ 9.62 (s, 1H), 7.29 (s, 1H), 7.03 (m, 1H), 6.91 (t, 1H), 6.84 (m, 1H), 4.03 (septet, 1H), 0.96 (d, 6H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 h, at which time TLC analysis
  3. dissolutionto dissolve all solids
  4. extractionthe mixture was extracted with ether (3x)
  5. washThe combined ether layer was washed with water, 2 M NaOH, again with water until clear (4x)
  6. dry with materialThe solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0e5684627b3747428380152ea872789a
Source dataset
uspto-grants-2002_10
Patent number
US06462092B1

Reaction notes

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