Acetic Acid → HCID 67983058, compound

HRID 718539Notes

Reaction equation

[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37](=O)[CH3:38])=[CH:31][CH:30]=1.CC(O)=O>C1COCC1>[CH3:38][C:37](=[CH:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:36][CH2:35][C:32]1[CH:31]=[CH:30][C:29]([OH:28])=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of benzyltriphenylphosphonium bromide (10.9 g, 25.1 mmol, 1.2 equiv.) in THF (35 mL), was added potassium-t-amylat (1.7 M in toluene, 20 mL, 34.0 mmol, 1.7 equiv.) at 25° C. 4-(4-Hydroxyphenyl)butan-2-one (3.3 g, 20.1 mmol, 1.0 equiv.) in THF (5 mL) was added to the red suspension, and the mixture was stirred at 70° C. for 30 min. After addition of 20% aq. AcOH-solution (10 mL) at 25° C., the aqueous layer was diluted with hexanes (50 mL). The organic phase was washed with H2O (2×30 mL) and MeOH/H2O (8:2, 2×20 mL) and concentrated. The residue was purified by flash chromatography on SiO2 to yield 2.10 g (44%) of the title compound as a white solid.

Workup

washThe organic phase was washed with H2O (2×30 mL) and MeOH/H2O (8:2, 2×20 mL)
concentrationconcentrated
customThe residue was purified by flash chromatography on SiO2

Sources & evidence

ORD record: ord-4af089b7f6c3466c8d6a1287e2e4f278
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

Loading…