1-Bromohexane → 1-(3-Hexyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone

HRID 1265245Notes

Reaction equation

HRID 1265245 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][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CS(C)=O>[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)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 81011-BromohexaneHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

Product 1

HCID 186150291-(3-Hexyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanoneYield 116.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone (0.103 g, 0.418 mmol) in DMSO (1 mL) was alkylated with bromohexane (0.097 g, 0.585 mmol, 0.082 mL) as described in Example 21. Aqueous workup gave 1(3-hexyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone 0.161 g (100% crude) as an orange oil: 1H-NMR (400 MHz, CDCl3) δ 7.74 (s, 1H, Ar-H), 6.82 (s, 1H, Ar-H), 4.02 (t, J=6.4 Hz, 2H, OCH2), 2.61 (s, 3H, CH3), 1.83 (m, 2H, CH2), 1.67 (app br d, 4H, 2CH2), 1.50 (m, 2H, CH2), 1.36 (m, 4H, 2CH2), 1.29 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3), 0.91 (t, J=7.0 Hz, 3H, CH3).

Sources & evidence

ORD record
ord-828be32b5b9341bf8e4f92598239f39a
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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