Potassium Carbonate → HCID 86657008, compound

HRID 337268Notes

Reaction equation

HRID 337268 reaction equation
[OH:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=1[CH2:15]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=1[CH2:15][O:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 118049533-Hydroxy-2-methoxybenzaldehyde

Product 1

HCID 86657008HCID 86657008, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 3-hydroxy-2-methoxybenzaldehyde (5.06 g, 32.7 mmol), 2,6-Dimethylbenzyl chloride (5.04 g, 33.1 mmol) and K2CO3 (4.78 g, 34.6 mmol) in dry DMF (15 ml) was stirred at room temperature under argon for 16 hours, then diluted with EtOAc (40 ml), and washed with water (20 ml). The organic layer was concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1) to give the title compound as an off white solid.

Workup

  1. washwashed with water (20 ml)
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 4:1)

Sources & evidence

ORD record
ord-ac13b45dbc5043b08aa11032d69cd6ac
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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