1-Butanol → HCID 19261375, compound

HRID 1808301Notes

Reaction equation

HRID 1808301 reaction equation
[Na].CN(C)C=O.Br[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12].Cl.[CH2:18]([OH:22])[CH2:19][CH2:20][CH3:21]>[Cu]Cl>[CH2:18]([O:22][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12])[CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 5

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 5360545Sodium

Product 1

HCID 19261375HCID 19261375, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

2.16 g (93.9 mmol) of sodium are dissolved in 15 ml of n-butanol at 110° C. for 3 hours. 20 ml of dimethylformamide are added at ambient temperature and then the medium is degassed several times. 3.4 g (34.1 mmol) of copper(I) chloride are added at ambient temperature and then the reaction medium is stirred for 10 minutes. 6.2 g (31 mmol) of 3-bromo-4-hydroxybenzaldehyde are added and then the reaction medium is stirred at 120° C. for 2 hours. The reaction mixture is cooled to ambient temperature and then the reaction is halted by the addition of 50 ml of a 2M hydrochloric acid solution. The medium is extracted with 250 ml of ethyl acetate. The solvents are evaporated and then the residue is filtered through a silica gel patch (2 cm): eluent heptane/ethyl acetate 8/2. After evaporation of the solvents, 5.55 g of orange oil are obtained. This oil is crystallized from pentane. 4.8 g of 3-butoxy-4-hydroxybenzaldehyde are obtained in the form of a brown solid after filtration.

Workup

  1. customthe medium is degassed several times
  2. stirringthe reaction medium is stirred at 120° C. for 2 hours
  3. extractionThe medium is extracted with 250 ml of ethyl acetate
  4. customThe solvents are evaporated
  5. filtrationthe residue is filtered through a silica gel patch (2 cm)
  6. customAfter evaporation of the solvents, 5.55 g of orange oil
  7. customare obtained
  8. customThis oil is crystallized from pentane

Sources & evidence

ORD record
ord-8904683165f44b2badb565948929854e
Source dataset
uspto-grants-2013_01
Patent number
US08357819B2

Reaction notes

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