4-Methyloxybenzyl chloride → 1-[3-(4-Methoxybenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalen-2-yl]-ethanone

HRID 1265264Notes

Reaction equation

HRID 1265264 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][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][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:23][CH:22]=1

Participants

3

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

Product 1

HCID 186150181-[3-(4-Methoxybenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalen-2-yl]-ethanoneYield 129.2%

Procedure

1-(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalen-2-yl)-ethanone (0.315 g, 1.28 mmol) was alkylated with 4-methoxybenzylchloride (0.280 g, 1.79 mmol, 0.24 mL) as described in Example 21. Aqueous workup gave 1-[3-(4-methoxybenzyloxy)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalen-2-yl]-ethanone 0.606 g (crude) as an orange oil: 1H-NMR (400 MHz, CDCl3) δ 7.74 (s, 1H, Ar—H), 7.39 (d of ABq, J=8.6 Hz, 2H), 6.92 (d of ABq, J=8.6 Hz, 2H), 6.91 (s, 1H, Ar—H), 5.06 (s, 2H, OCH2), 3.82 (s, 3H, OCH3), 2.55 (s, 3H, CH3), 1.67 (m, 4H, 2CH2), 1.27 (s, 6H, 2CH3), 1.26 (s, 6H, 2CH3).

Sources & evidence

ORD record
ord-65abaa49798b4561933e192524a75e75
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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