3-Hydroxybenzoic Acid → HCID 16578051, compound

HRID 1790776Notes

Reaction equation

HRID 1790776 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-c1b5f9b9749241d99f999a1d1f16fad0
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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