Hydrochloric Acid → HCID 15124025, compound

HRID 1084873Notes

Reaction equation

HRID 1084873 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].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[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:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([Cl:21])=[CH:23][CH:24]=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 85014-Chlorobenzoyl chloride2×HCID 6451240Aluminum(III) Chloride2×HCID 15124018HCID 15124018, compound2×

Product 1

HCID 15124025HCID 15124025, 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 p-chlorobenzoyl chloride (0.793 g, 4.53 mmol) in 1,2-dichloroethane (40 mL) at 0° C. was added aluminum chloride (0.604 g, 4.53 mmol) and the mixture heated to reflux for two hours. Additional portions of 4-chlorobenzoyl chloride (0.475 g, 2.71 mmol) and aluminum chloride (0.362 g, 2.71 mmol) were added and the reflux continued for an additional 1.5 hours. The reaction mixture was poured into 2N HCl (100 mL) and extracted with methylene chloride (4×25 mL). The combined extracts were washed with water (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-p-chlorobenzoylbenzofuran-2-carboxylate, compound 17 as an oil sufficiently pure for further chemistry. 1H NMR d 1.34 (3H, t, J=6 Hz), 1.50 (9H, s), 2.88 (3H, s), 4.54 (2H, q, J=6 Hz), 7.47 (2H, d, J=8 Hz), 7.78 (2H, d, J=8 Hz), 7.87 (1H, s).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for two hours
  3. extractionextracted with methylene chloride (4×25 mL)
  4. washThe combined extracts were washed with water (25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-db7e40b003d44f778e241fec4920a8ab
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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