3-Hydroxybenzaldehyde → HCID 21949743, compound

HRID 2215172Notes

Reaction equation

HRID 2215172 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH2:23][CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(OCC)(=O)C>CN(C)C=O>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH:17]([CH2:23][CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 79039Butanoic acid, 2-bromo-, ethyl ester

Product 1

HCID 21949743HCID 21949743, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxybenzaldehyde (18.3 g, 0.150 mol) was dissolved in N,N-dimethylformamide (150 mL). Subsequently, potassium carbonate (22.80 g, 0.165 mol), and then ethyl 2-bromobutyrate (29.26 g, 0.150 mol) were added thereto, and the resultant mixture was stirred overnight at 80° C. The temperature of the reaction mixture was returned to room temperature. Ethyl acetate was added. Washing was performed sequentially with water and brine, followed by drying over sodium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=5/1), whereby a colorless oil was obtained (35.29 g, 0.149 mol, 99.6%).

Workup

  1. customwas returned to room temperature
  2. washWashing
  3. dry with materialby drying over sodium sulfate
  4. filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=5/1), whereby a colorless oil
  5. customwas obtained (35.29 g, 0.149 mol, 99.6%)

Sources & evidence

ORD record
ord-85a27525aa1e43b289faddcc20ff9da5
Source dataset
uspto-grants-2006_09
Patent number
US07109226B2

Reaction notes

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