2-Butene, 1-bromo-3-methyl- → 1-[3-(3-Methylbut-2-enyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone

HRID 1265246Notes

Reaction equation

HRID 1265246 reaction equation
[OH:1][C:2]1[C:3]([C:16](=[O:18])[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.Br[CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]>CS(C)=O>[CH3:23][C:22]([CH3:24])=[CH:21][CH2:20][O:1][C:2]1[C:3]([C:16](=[O:18])[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

Product 1

HCID 186149261-[3-(3-Methylbut-2-enyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanoneYield 126.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-ethanone (0.125 g, 0.507 mmol) in DMSO (1 mL) was alkylated with 4-bromo-2-methyl-2-butene (0.106 g, 0.710 mmol, 0.082 mL) as described in Example 21. Aqueous workup gave 1-[3-(3-methylbut-2-enyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone 0.201 g (100% crude) as a clear yellow crystalline solid: 1H-NMR (400 MHz, CDCl3) δ 7.72 (s, 1H, Ar-H), 6.83 (s, 1H, Ar-H), 5,48 (m, 1H, olefinic), 4.59 (d, J=6.6 Hz, 2H, OCH2), 2.60 (s, 3H, CH3), 1.79 (s, 3H, CH3), 1.76 (s, 3H, CH3), 1.67 (appp d, J=2.7 Hz, 4H, 2CH2), 1.28 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3).

Sources & evidence

ORD record
ord-b1dfbd9b91c9416da67f34d6a7f17549
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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