Hydrochloric Acid → HCID 67366816, compound

HRID 410026Notes

Reaction equation

HRID 410026 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:22])[CH2:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1.Cl>O1CCOCC1>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:22])[CH2:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67367535HCID 67367535, compound

Product 1

HCID 67366816HCID 67366816, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 4-(2-(2,4-dihydroxyphenyl)-2-oxoethyl)benzoate (2 g, 6.7 mmol) in 1,4-dioxane (10 ml), was added conc. HCl (10 ml). The reaction mixture was stirred at 70° C. overnight. The volatiles were removed under reduced pressure. The residue was dissolved with water (20 ml) and extracted with EtOAc (20 ml×2). The combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated to afford product as a brown solid (1.5 g, 83.3%). MS (ESI): m/z 273.1 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionThe residue was dissolved with water (20 ml)
  3. extractionextracted with EtOAc (20 ml×2)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d33750a964ef4941b29b6e26872cb919
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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