3-Hydroxybenzoic Acid → HCID 16578051, compound

HRID 489022Notes

Reaction equation

HRID 489022 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[K].CC(C)([O-])C.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1)=[O:6]

Participants

5

Reactant 3

HCID 74203-Hydroxybenzoic AcidHCID 699934-Methyloxybenzyl chlorideHCID 50987170Potassium tertbutoxide

Product 1

HCID 16578051HCID 16578051, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxybenzoic acid (6.9 g, 50 mmole) in DMF (100 ml) was added potassium-tert.-butoxide (6.17 g, 55 mmole) and the mixture was stirred at room temperature for one hour. 4-Methoxybenzyl chloride (9.4 g, 60 mmole) was added and the mixture was stirred for 16 hours at 60° C. The mixture was evaporated under reduced pressure and ethyl acetate (250 ml) were added. The organic phase was washed five times with water, dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography with toluene/acetone. Yield: 10.5 g=81%

Workup

  1. stirringthe mixture was stirred for 16 hours at 60° C
  2. customThe mixture was evaporated under reduced pressure and ethyl acetate (250 ml)
  3. additionwere added
  4. washThe organic phase was washed five times with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe product was isolated by silica gel column chromatography with toluene/acetone

Sources & evidence

ORD record
ord-ddd78620f11e4bff9d99cc2726d1549b
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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