Isopropyl iodide → 4-(Benzyloxy)-2-isopropoxybenzaldehyde

HRID 1805922Notes

Reaction equation

HRID 1805922 reaction equation
C([O-])([O-])=O.[K+].[K+].I[CH:8]([CH3:10])[CH3:9].[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[C:21]([OH:27])[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C.O>[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[C:21]([O:27][CH:8]([CH3:10])[CH3:9])[CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 106357444-(Benzyloxy)-2-isopropoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

K2CO3 (6.14 g, 44.4 mmol) and 2-iodopropane (1.28 mL, 12.76 mmol) were added successively to a stirred solution of 4-benzyloxy-2-hydroxybenzaldehyde (2.33 g, 10.21 mmol) in dry DMF (12.8 mL) at 25° C. under N2. The reaction was heated at 50° C. overnight. The reaction was diluted with water (50 mL) and extracted with Et2O (3×50 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the crude product. This was azeotroped from toluene to afford 4-(benzyloxy)-2-isopropoxybenzaldehyde. LCMS calc.=293.1; found=292.9 (M+Na)+.

Workup

  1. extractionextracted with Et2O (3×50 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product
  5. customThis was azeotroped from toluene

Sources & evidence

ORD record
ord-6d1ffc315c6a4d248a1731c38bf7273d
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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