Benzyl Bromide → 1-(3-Benzyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone

HRID 1265247Notes

Reaction equation

HRID 1265247 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.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O>[CH2:19]([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)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

Product 1

HCID 186149941-(3-Benzyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanoneYield 75.4%

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 benzylbromide (0.100 g, 0.585 mmol, 0.070 mL) as described in Example 21. Aqueous workup gave 1-(3-benzyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone 0.106 g (75% crude) as a yellow oil: 1H-NMR (400 MHz, CDCl3) δ 7.74 (s, 1H, ArH), 7.45 (m, 5H, ArH), 6.88 (s, 1H, ArH), 5.12 (s, 2H, OCH2), 2.59 (s, 3H, CH3), 1.66 (br s, 4H, 2CH2), 1.28 (s, 6H, 2CH3), 1.25 (s, 6H, 2CH3).

Sources & evidence

ORD record
ord-fac41dc008864e31b10c23c9d4ed2aba
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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