3-Hydroxybenzaldehyde → 3-Isopropoxybenzaldehyde

HRID 501732

Reaction equation

HRID 501732 reaction equation
FC(F)(F)C(N[C@@H:6]1[C:14]2C(=CC=C(OC)C=2)C(=O)[CH2:7]1)=O.[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25].IC(C)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:6]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25])([CH3:14])[CH3:7]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6362Isopropyl iodide2×HCID 11430Potassium Carbonate2×HCID 1472787(S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide

Product 1

HCID 7129143-IsopropoxybenzaldehydeYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Step AU (1). A solution of 3-hydroxybenzaldehyde (67 g, 549 mmol), 2-iodopropane (100 g, 588 mmol) and K2CO3 (130 g, 942 mmol) in 400 mL DMF was stirred for 18 h. To the above solution was added 2-iodopropane (20 g, 117 mmol) and K2CO3 (20 g, 145 mmol) and the mixture was stirred for another 24 h. The reaction mixture was poured into 300 mL water which was extracted with EtOAc (200 mL×3). The combined organic layers were washed with water (100 mL×3), dried over Na2SO4, filtered, and concentrated in vacuo to afford 77 g (85% yield) of 3-isopropoxybenzaldehyde as an oil. 1H NMR (300 MHz, CDCl3) δ 1.29-1.31 (d, 6H) 4.5-4.6 (m, 1H) 7.0-7.1 (m, 1H) 7.3-7.4 (m, 3H).

Workup

  1. extractionwas extracted with EtOAc (200 mL×3)
  2. washThe combined organic layers were washed with water (100 mL×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8571272274344ffcbf958067fbe99d83
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Linked notes

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