(+-)-2-Butanol → (+/-)5-sec-Butoxymethyl-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one

HRID 496405Notes

Reaction equation

HRID 496405 reaction equation
Cl[CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14].C(N(CC)CC)C.[CH3:22][CH:23]([OH:26])[CH2:24][CH3:25]>>[CH:23]([O:26][CH2:2][C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:14])([CH2:24][CH3:25])[CH3:22]

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 8471TriethylamineHCID 123936195-(chloromethyl)-6-hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 22325010(+/-)5-sec-Butoxymethyl-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Procedure

According to step (a) in the method of example A, 5-Chloromethyl-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (0.211 g, 1.0 mmol) was combined with triethylamine (0.167 ml, 1.2 mmol) in (±)butan-2-ol (3 ml, Aldrich Chemical) to produce 159 mg of desired product as an orange oil. Low resolution mass spectrum (APCI) m/z 249 [M+H]+.

Sources & evidence

ORD record
ord-e7d7ec0f7d0f40668d20c5af8cc9866a
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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