Hydrochloric Acid → HCID 86730352, compound

HRID 1427051Notes

Reaction equation

HRID 1427051 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][CH3:6].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12].C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)C=O.O.C(OCC)(=O)C>[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:2][CH2:3][CH2:4][O:5][CH3:6])[CH:11]=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 87683,4-DihydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 86730352HCID 86730352, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Commercially available 1-bromo-3-methoxypropane (24.0 g, 157 mmol) was added to a solution of commercially available 3,4-dihydroxybenzaldehyde (21.7 g, 157 mmol) and sodium carbonate (25.0 g, 236 mmol) in N,N-dimethylformamide (50 mL) under nitrogen atmosphere at room temperature. The reaction liquid was stirred at room temperature for 3 days and 4 hours. 2 M hydrochloric acid, ethyl acetate, and water were added to the reaction liquid at 0° C. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed serially with water and a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and the filtrate was concentrated under vacuum. The insoluble matters were separated by filtration with dichloromethane and the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1) to obtain the title compound (17.2 g, 52%).

Workup

  1. customThe reaction liquid
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed serially with water
  4. dry with materiala saturated saline solution and then dried over anhydrous sodium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe insoluble matters were separated by filtration with dichloromethane
  8. concentrationthe filtrate was concentrated under vacuum
  9. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1)

Sources & evidence

ORD record
ord-11c4ff8b2cd64603a5c5920bf4928fb8
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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