Hydrochloric Acid → HCID 15124013, compound

HRID 1084865Notes

Reaction equation

HRID 1084865 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[CH:8][CH:9]=[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]=2[O:4][C:3]=1C(O)=O.N1C2C(=CC=CC=2)C=CC=1.Cl>[Cu].C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[CH:8][CH:9]=[C:10]([C:11]([CH3:13])([CH3:12])[CH3:14])[C:5]=2[O:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 15124011HCID 15124011, compound

Product 1

HCID 15124013HCID 15124013, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 3-methyl-4-hydroxy-7-tert-butylbenzofuran-2-carboxylic acid (0.250 g, 1.0 mmol), quinoline (0.75 mL), and copper powder (0.064 g, 1.0 mmol) was heated to 210° C. until gas evolution ceased (about 10 minutes) and then poured into 2N HCl (15 mL). Carbon tetrachloride (15 mL) was added and the biphasic mixture was filtered through celite. The layers were separated and the aqueous layer extracted with an additional portion of carbon tetrachloride (15 mL). The combined extracts were dried (Na2SO4) and concentrated. Flash chromatography using 10% ethyl acetate in hexane as eluant afforded 3-methyl-4-hydroxy-7-tert-butylbenzofuran, compound 10a. Recrystallization from hexane provided analytically pure material. 1H NMR d 1.46 (9H, s), 2.43 (3H, s), 6.49 (1H, d, J=8 Hz), 6.98 (1H, d, J=8 Hz), 7.36 (1H, s).

Workup

  1. custom(about 10 minutes)
  2. filtrationthe biphasic mixture was filtered through celite
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with an additional portion of carbon tetrachloride (15 mL)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5419b0893742447ebd042714efc40a79
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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