Potassium Carbonate → 4-(2-Tetrahydropyranylmethoxy)-1-naphthaldehyde

HRID 1166722Notes

Reaction equation

HRID 1166722 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[CH2:15][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 3442904-Hydroxy-1-naphthaldehyde

Product 1

HCID 229992594-(2-Tetrahydropyranylmethoxy)-1-naphthaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-hydroxynaphthaldehyde (1 g, 5.8 mmol), 2-bromomethyl tetrahydropyran (1 g, 5.8 mmol) and powdered K2CO3 (1.2 g, 8.7 mmol) in dimethyl formamide was stirred at 60° C. overnight. The mixture was taken up in water and ethyl acetate. The organic layer was separated and washed with water, brine, dried over MgSO4, filtered, and concentrated. The product was purified by silica gel column chromatography using ethyl acetate/hexane.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6ae341a9fe754b399a0839803941ce30
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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