Butyric Acid → 4-Butanoylresorcinol

HRID 2379171

Reaction equation

HRID 2379171 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](O)(=[O:13])[CH2:10][CH2:11][CH3:12].Cl.[Cl-].[Na+].O>ClCCCl.[Cl-].[Cl-].[Zn+2]>[C:9]([C:6]1[CH:7]=[CH:8][C:1]([OH:2])=[CH:3][C:4]=1[OH:5])(=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 264Butyric AcidHCID 5054ResorcinolHCID 131718760Hydrochloric acid brine

Product 1

HCID 781034-Butanoylresorcinol

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of resorcinol (1.5 g) and butyric acid (2.9 mL) in 1,2-dichloroethane (45 mL) was added ZnCl2 (3.22 g) and the mixture then heated at 150° C. under nitrogen for 5 hr. The reaction mixture was cooled, poured onto 1N HCl/brine and extracted (3x EtOAc). After washing with 0.1N K2CO3, then twice with brine, the organic layer was dried and evaporated. Chromatography of the residue (silica gel; hexane/EtOAc 2:1) afforded the title product as a solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted (3x EtOAc)
  3. washAfter washing with 0.1N K2CO3
  4. dry with materialtwice with brine, the organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-bf0c04924124472d9d82c72dd027406c
Source dataset
uspto-grants-1994_11
Patent number
US05360815

Linked notes

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