4-Chloro-1-butanol → HCID 23089343, compound

HRID 2222055Notes

Reaction equation

HRID 2222055 reaction equation
[CH2:1]([O:5]C1C=C2C(=CC=1)C=C([Mg]Br)C=C2)[CH2:2][CH2:3][CH3:4].[Mg].[CH2:19]([O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([SH:34])[CH:28]=[CH:27]2)[CH2:20][CH2:21][CH3:22].ClCCCCO>CC(C)=O.O.C(OCC)(=O)C.C(N(CC)CC)C>[OH:5][CH2:1][CH2:2][CH2:3][CH2:4][S:34][C:29]1[CH:28]=[CH:27][C:26]2[C:31](=[CH:32][CH:33]=[C:24]([O:23][CH2:19][CH2:20][CH2:21][CH3:22])[CH:25]=2)[CH:30]=1

Participants

9

Reactant 4

HCID 135694-Chloro-1-butanolHCID 5462224MagnesiumHCID 16038058HCID 16038058, compoundHCID 178450078HCID 178450078, compound

Product 1

HCID 23089343HCID 23089343, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

30 g 6-n-butoxy-2-naphthalene thiol was obtained by the method of non-patent document 5 from 72 g of 2-bromo-6-n-butoxy naphthalene prepared according to the method described in J. Am. Chem. Soc., Vol. 118, P. 6841-6852 (1996) and 6-n-butoxy-2-naphthyl magnesium bromide prepared from 7.5 g of magnesium. Next, 30 g of 6-n-butoxy-2-naphthalene thiol was dissolved in 150 ml of acetone and 14.0 g of 4-chloro-1-butanol was added to the solution. After the addition of 26.1 g of triethylamine dropwise over 15 minutes, the mixture was reacted for 15 hours at room temperature while stirring. Next, 150 ml of ethyl acetate and 150 ml of water were added to the reaction mixture. After removing the water layer using a separating funnel, the organic layer was washed three times with 75 ml of a 10 wt % sodium carbonate aqueous solution, then repeatedly washed with 5 wt % oxalic acid aqueous solution until the water layer becomes pH 2. Then, the organic layer was washed with purified water until the water layer becomes pH 7 and dried using magnesium sulfate. After drying, magnesium sulfate was removed by filtration and the solvent was evaporated using a rotary evaporator at 40° C. under reduced pressure by a stream aspirator to obtain 29.4 g of 4-hydroxybutyl-(6-n-butoxynaphthalen-2-yl)sulfide, of which the purity determined by high performance liquid chromatography (HPLC) was 95 wt % or more.

Workup

  1. customprepared
  2. customthe mixture was reacted for 15 hours at room temperature
  3. customAfter removing the water layer
  4. washthe organic layer was washed three times with 75 ml of a 10 wt % sodium carbonate aqueous solution
  5. washrepeatedly washed with 5 wt % oxalic acid aqueous solution until the water layer
  6. washThen, the organic layer was washed with purified water until the water layer
  7. customdried
  8. customAfter drying
  9. custommagnesium sulfate was removed by filtration
  10. customthe solvent was evaporated
  11. customa rotary evaporator at 40° C. under reduced pressure by a stream aspirator

Sources & evidence

ORD record
ord-80c90138ad3946b79ae0a0caca4e57e9
Source dataset
uspto-grants-2008_05
Patent number
US07371503B2

Reaction notes

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