Hexane → HCID 23114103, compound

HRID 2376317Notes

Reaction equation

HRID 2376317 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[OH:22][C:23]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[C:24]=1[CH:25]=[O:26]>C1COCC1.O>[OH:26][CH:25]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1)[C:24]1[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[CH:30][C:23]=1[OH:22]

Participants

7

Reactant 4

HCID 8058HexaneHCID 114621-Bromo-4-isopropylbenzeneHCID 591070HCID 591070, compoundHCID 178418339Butyllithium

Product 1

HCID 23114103HCID 23114103, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-4-isopropylbenzene (3.32 g, 16.7 mmol) in THF (30 mL) was added dropwise n-butyllithium (a 1.59 M hexane solution, 9.2 mL, 14.7 mmol) under argon atmosphere at −78° C. The reaction solution was stirred for 30 minutes, a solution of 2-hydroxy-4,6-dimethylbenzaldehyde obtained in Reference Example 146 (1.0 g, 6.7 mmol) in THF (10 mL) was added dropwise thereto at −78° C., and the mixture then was stirred for 30 minutes. The reaction solution was warmed to room temperature, water was added thereto to separate the organic layer, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 1.64 g (yield 91%) of the title compound. Melting point: 103-104° C. (ethyl acetate-hexane).

Workup

  1. additionwas added dropwise
  2. stirringat −78° C., and the mixture then was stirred for 30 minutes
  3. customto separate the organic layer
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-2cf9160d1be74ccdb70a1575fbdd14d3
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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