1-Bromo-2-methylpropane → HCID 18614997, compound

HRID 1265263Notes

Reaction equation

HRID 1265263 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)[CH:20]([CH3:22])[CH3:21]>>[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)[CH:20]([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 65551-Bromo-2-methylpropaneHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

Product 1

HCID 18614997HCID 18614997, compoundYield 105.4%

Procedure

1-(3-Hydroxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalen-2-yl)-ethanone (0.250 g, 1.01 mmol) was alkylated with isobutylbromide (0.195 g, 1.42 mmol, 0.154 mL) as described in Example 21. Aqueous workup gave 1-[3-isobutyloxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-naphthalen-2-yl]-ethanone 0.322 g (crude) as an orange oil: 1H-NMR (400 MHz, CDCl3) δ 7.74 (s, 1H, Ar—H), 6.81 (s, 1H, Ar—H), 4.13 (d, J=6.2 Hz, 2H, OCH2), 2.62 (s, 3H, CH3), 2.16 (m, 1H, CH), 1.68 (app br d, 4H, 2CH2), 1.30 (s, 6H, 2CH3), 1.28 (s, 6H, 2CH3), 1.08 (d, J=6.7 Hz, 6H, 2CH3).

Sources & evidence

ORD record
ord-697c7965b6934715b0cdbcce3bc9cbb5
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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