Hydrochloric Acid → HCID 15124022, compound

HRID 1084871Notes

Reaction equation

HRID 1084871 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[CH3:1][C:2]1[C:6]2[C:7]([OH:15])=[C:8]([C:11]([CH3:14])([CH3:12])[CH3:13])[CH:9]=[C:10]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:5]=2[O:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15124018HCID 15124018, compound2×

Product 1

HCID 15124022HCID 15124022, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl 3-methyl-4-hydroxy-5-tert-butylbenzofuran-2-carboxylate, compound 12a (1.00 g, 3.62 mmol) and benzoyl chloride (0.763 g, 5.43 mmol) in 1,2-dichloroethane (40 mL) at 0° C. was added aluminum chloride (0.720 g, 5.43 mmol) and the resulting mixture warmed to reflux for 3.5 hours. The reaction was allowed to cool, poured into 2N HCl (100 mL) and extracted with methylene chloride (4×25 mL). The combined extracts were washed with 5% NaHCO3 (25 mL), dried (Na2SO4), and concentrated. Flash chromatography using 25% ethyl acetate in hexane as eluant afforded ethyl 3-methyl-4-hydroxy-5-tert-butyl-7-benzoylbenzofuran-2-carboxylate, compound 15 as an oil sufficiently pure for further chemistry. 1H NMR d 1.34 (3H, t, J=6 Hz), 1.51 (9H, s), 2.89 (3H, s), 4.35 (2H, q, J=6 Hz), 7.56 (3H, m), 7.86 (3H, m).

Workup

  1. temperaturethe resulting mixture warmed
  2. temperatureto reflux for 3.5 hours
  3. temperatureto cool
  4. extractionextracted with methylene chloride (4×25 mL)
  5. washThe combined extracts were washed with 5% NaHCO3 (25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-50946377d8be46a18367b4c9a56b23e9
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

Loading…