Dimethylformamide → HCID 82926311, compound

HRID 871045Notes

Reaction equation

HRID 871045 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].CN(C=O)C.Cl[CH2:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20].C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 107585Pentane, 3-(chloromethyl)-

Product 1

HCID 82926311HCID 82926311, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
120 °C

Procedure

To a solution of 5-chloro-2-hydroxybenzaldehyde, 2.1 g (13.4 mmol) DMF (50 mL) under N2 atmosphere at RT was added 3-(chloromethyl)pentane (1.92 g 15.6 mmol), K2CO3 (4.5 g, 32.6 mmol) and tetrabutylammonium iodide (0.35 g, 0.9 mmol). The resulting mixture was stirred at 120° C. for 5 hours. The mixture was partitioned between water (80 ml) and EtOAc (80 ml). The organic layer was washed with water (80 ml) followed by brine (80 ml), dried over (Na2SO4), filtered and the volatiles were removed in vacuo. The crude product was purified on silica to yield to yield 2.83 g of 5-Chloro-2-(2-ethyl-butoxy)-benzaldehyde, 1.

Workup

  1. customThe mixture was partitioned between water (80 ml) and EtOAc (80 ml)
  2. washThe organic layer was washed with water (80 ml)
  3. dry with materialdried over (Na2SO4)
  4. filtrationfiltered
  5. customthe volatiles were removed in vacuo
  6. customThe crude product was purified on silica
  7. customto yield

Sources & evidence

ORD record
ord-0b490fa8fa24488ab026a27d1e58aafa
Source dataset
uspto-grants-2015_03
Patent number
US08969589B2

Reaction notes

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