3,4-Dihydroxybenzaldehyde → HCID 89155844, compound

HRID 591322Notes

Reaction equation

HRID 591322 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH2:21]([O:20][CH2:19][CH2:18][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[OH:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 73833Benzene, ((2-bromoethoxy)methyl)-

Product 1

HCID 89155844HCID 89155844, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of commercially available 3,4-dihydroxybenzaldehyde (17.04 g, 123.7 mmol) in 150 ml DMF and 14.9 g (107.5 mmol) potassium carbonate was stirred at 60° C. for 4 hours. 30.8 g (14.2 mmol) [(2-bromoethoxy)methyl]benzene was added at room temperature. The reaction mixture was stirred over night. The volume of the reaction mixture is reduced to half volume in vacuo. Aqueous saturated ammonium chloride solution and ethyl acetate is added to the reaction mixture. The organic phase is separated, washed twice with saturated aqueous sodium chloride solution, dried with magnesium sulfate filtered and concentrated in vacuo. The crude product is purified by column chromatography (silica gel, hexane/ethylacetate gradient: 7:1→1:2). The desired product was obtained in 22.2% yield (8.27 g, 27.3 mmol).

Workup

  1. customThe organic phase is separated
  2. washwashed twice with saturated aqueous sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, hexane/ethylacetate gradient: 7:1→1:2)

Sources & evidence

ORD record
ord-4b25d7fac3fb45698626824051e4321f
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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