4-Methylbenzyl chloride → 1-[3-(4-Methylbenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone

HRID 1265248Notes

Reaction equation

HRID 1265248 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.[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>>[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:1][C:2]2[C:3]([C:16](=[O:18])[CH3:17])=[CH:4][C:5]3[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=3[CH:11]=2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 77224-Methylbenzyl chlorideHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

Product 1

HCID 186149931-[3-(4-Methylbenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanoneYield 131.4%

Procedure

1-(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone (0.116 g, 0.471 mmol) was alkylated with 4-methylbenzylchloride (0.93 g, 0.659 mmol, 0.087 mL) as described in Example 21. Aqueous workup gave 1-[3(4-Methylbenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl]ethanone 0.217 g (131% crude) as a pale orange solid: 1H-NMR (400 MHz, CDCl3) δ 7.74 (s, 1H, ArH), 7.33 and 7.20 (d, of ABq, J=7.8 Hz, 4H, Ar-H), 6.91 (s, 1H, ArH), 5.08 (s, 2H, OCH2), 2.56 (s, 3H, CH3), 2.35 (s, 3H, ArCH3), 1.66 (br s, 4H, 2CH2), 1.28 (s, 6H, 2CH3), 1.25 (s, 6H, 2CH3).

Sources & evidence

ORD record
ord-ad831184d70f43a3bbbc51b546bbc6aa
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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