Hydrochloric Acid → HCID 15124027, compound

HRID 1084875Notes

Reaction equation

CC1C2C(O)=C(C(C)(C)C)C=CC=2OC=1.ClC1C=CC(C(C2C3OC(C(O)=O)=CC=3C=CC=2)=O)=CC=1.[CH3:37][C:38]1[C:42]2[C:43]([OH:60])=[C:44]([C:56]([CH3:59])([CH3:58])[CH3:57])[CH:45]=[C:46]([C:47](=[O:55])[C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=3)[C:41]=2[O:40][C:39]=1C(O)=O.N1C2C(=CC=CC=2)C=CC=1.Cl>[Cu].C(OCC)(=O)C>[CH3:37][C:38]1[C:42]2[C:43]([OH:60])=[C:44]([C:56]([CH3:58])([CH3:57])[CH3:59])[CH:45]=[C:46]([C:47](=[O:55])[C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=3)[C:41]=2[O:40][CH:39]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 3-methyl-4-hydroxy-5-tert-butylbenzofuran-7-p-chlorobenzoylbenzofuran-2-carboxylic acid, compound 18 (0.281 g, 0.73 mmol), copper (0.046 g, 0.73 mmol), and quinoline (1 mL) was heated to 160° C. until gas evolution had ceased. The reaction mixture was allowed to cool and poured into 2N HCl (25 mL). Ethyl acetate (25 mL) was added and the mixture was filtered through a pad of celite. The layers were separated and the aqueous layer reextracted with ethyl acetate (2×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Flash chromatography using 10% ethyl acetate as eluant afforded 3-methyl-4-hydroxy-5-tert-butyl-7-p-chlorobenzoylbenzofuran, compound 19 as an oil which solidified on standing. 1H NMR d 1.50 (9H, s), 2.50 (3H, d, J=2 Hz), 5.79 (1H, s), 7.30 (1H, s), 7.46 (2H, d, J= 8 Hz), 7.66 (1H, s), 7.79 (2H, d, J=8 Hz).

Workup

temperatureto cool
filtrationthe mixture was filtered through a pad of celite
customThe layers were separated
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-c020cc9cb0ad40d2b2a767bcd1580380
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006549

Reaction notes

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