Hydrochloric Acid → 2-Acetyl-4-(2-hydroxy-3,5-di-tert-butylphenyl)benzo[b]thiophene

HRID 1394598Notes

Reaction equation

[C:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:14]=3[O:27]COC)[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].Cl>C1COCC1>[C:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:21])([CH3:20])[CH3:22])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:14]=3[OH:27])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A slurry of 365 mg (0.859 mmol) of 2-acetyl-4-(2-methoxymethoxy-3,5-di-tert-butylphenyl)benzo[b]thiophene into a mixture of 5 mL of THF and 5 mL of aqueous 6N HCl was heated to 50° C. overnight. After cooling, the THF was evaporated and the aqueous solution was extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated under reduced pressure. The crude 2-acetyl-4-(2-hydroxy-3,5-di-tert-butylphenyl)benzo[b]thiophene was directly used in the next step. 1H-NMR (CDCl3), δ: 7.92 (d, J=8.0 Hz, 1H), 7.73 (s, 1H), 7.58 (t, J=7.4 Hz, 1H), 7.47 (d, J=2.6 Hz, 1H), 7.42 (d, J=2.3 Hz, 1H), 7.14 (d, J=2.4 Hz, 1H), 5.03 (s, 1H), 2.57 (s, 3H), 1.48 (s, 9H), 1.34 (s, 9H).

Workup

temperatureAfter cooling
customthe THF was evaporated
extractionthe aqueous solution was extracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-e4589b8ede4e45ff8815d0f5ec59affe
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348359B2

Reaction notes

Loading…