Hydrochloric Acid → HCID 15124014, compound

HRID 1084866Notes

Reaction equation

HRID 1084866 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:19])=[C:8]([C:15]([CH3:18])([CH3:17])[CH3:16])[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>C(OCC)(=O)C.[Cu]>[CH3:1][C:2]1[C:6]2[C:7]([OH:19])=[C:8]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[C:10]([C:11]([CH3:12])([CH3:14])[CH3:13])[C:5]=2[O:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 15124012HCID 15124012, compound

Product 1

HCID 15124014HCID 15124014, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 3-methyl-4-hydroxy-5,7-di-tert-butylbenzofuran-2-carboxylic acid (0.350 g, 1.14 mmol), quinoline (1.0 mL), and copper powder (0.072 g 1.14 mmol) was heated to 210° C. until gas evolution had ceased. The mixture was cooled, diluted with ethyl acetate (30 mL) and poured into 2N HCl. The biphasic mixture was filtered through a celite pad and the layers separated. The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic layers dried (Na2SO4) and concentrated. Flash chromatography afforded 3-methyl-4-hydroxy-5,7-di-tert-butylbenzofuran, compound 10b. 1H NMR d 1.46 (9H, s), 1.49 (9H, s), 2.46 (3H, s), 5.12 (1H, s), 7.11 (1H, s), 7.29 (1H, s).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe biphasic mixture was filtered through a celite pad
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
  5. dry with materialthe combined organic layers dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1ace1187193648ad878a215874b36c6c
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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