O-Cresol → 4-[1-(4-Bromophenyl)-1-ethylpropyl]-2-methylphenol

HRID 250178Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[C:14]1([CH3:21])[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][CH:15]=1.OS(O)(=O)=O>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([OH:20])=[C:14]([CH3:21])[CH:15]=2)([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of 3-(4-bromophenyl)-pentan-3-ol (2.45 g, 10 mmol) and o-cresol 1.05 mL, 10.2 mmol) in H2O (1.0 mL) chilled to 0° C. was added conc H2SO4 (4.0 g) dropwise. After 1.5 h the reaction mixture was diluted with H2O (50 mL) and extracted with Et2O (2×50 mL). The combined extracts were washed with water, satd NaHCO3, and brine, then dried (anhyd Na2SO4) and concentrated under reduced pressure. The resulting crude product was chromatographed (silica, EtOAC/Hex, 0:100 to 10:90) to afford the title compound (2.1 g, 64% non-optimized) as a colorless liquid: 1H-NMR (CDCl3) δ 7.36 (2H, d, J=8.6), 7.05 (2H, d, J=8.6), 6.83-6.88 (2H, m), 6.67 (1H, d, J=8.1), 4.52 (1H, br s), 2.20 (3H, s), 2.04 (4H, q, J=7.3), 0.61 (6H, t, J=7.3).

Workup

extractionextracted with Et2O (2×50 mL)
washThe combined extracts were washed with water
dry with materialdried (anhyd Na2SO4)
concentrationconcentrated under reduced pressure
customThe resulting crude product was chromatographed (silica, EtOAC/Hex, 0:100 to 10:90)

Sources & evidence

ORD record: ord-7771b4b352bd4418bc8db9378a282ce5
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863298B2

Reaction notes

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