Potassium Carbonate → HCID 59277541, compound

HRID 1362373Notes

Reaction equation

HRID 1362373 reaction equation
[C:1]([C:5]1[C:6]([OH:13])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].I[CH2:21][CH2:22][CH3:23]>CN(C=O)C.O>[C:1]([C:5]1[C:6]([O:13][CH2:21][CH2:22][CH3:23])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 59277541HCID 59277541, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-tert-butyl-2-hydroxy-benzaldehyde (2.04 g, 11.5 mmol) and K2CO3 (7.91 g, 57.3 mmol) in anhydrous DMF (23 ml) was added 1-iodopropane (2.34 ml, 24.0 mmol). The reaction mixture was left to stir for 48 h at room temperature. The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (3×50 ml). Combined organic layers were washed with water (50 ml) and brine (50 ml), dried over MgSO4, filtered and the solvent was removed in vacuo to give a yellow oil. Purification by column chromatography (silica gel, gradient elution of hexanes to 20% EtOAc/hxanes) gave 3-tert-butyl-2-propoxy-benzaldehyde (2.55 g, 99%) as a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ 10.21 (s, 1H), 7.62 (s, 1H), 7.61 (s, 1H), 7.19 (t J=8.0, 1H), 3.89 (t, J=8.0 Hz, 2H), 1.91-1.82 (m, 2H), 1.37 (s, 9H), 1.03 (t, J=8.0 Hz, 3H).

Workup

  1. waitThe reaction mixture was left
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washCombined organic layers were washed with water (50 ml) and brine (50 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customto give a yellow oil
  8. customPurification
  9. washby column chromatography (silica gel, gradient elution of hexanes to 20% EtOAc/hxanes)

Sources & evidence

ORD record
ord-6309e01c11a94048942b4c88deba7601
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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