Hydrochloric Acid → HCID 86722739, compound

HRID 1525794Notes

Reaction equation

HRID 1525794 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=[O:8])[CH:2]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].Cl>O1CCCC1>[CH2:10]([C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[C:7]([OH:9])=[O:8])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74183-Methylbenzoic acidHCID 123941-BromopentadecaneHCID 2724682Lithium diisopropylamide

Product 1

HCID 86722739HCID 86722739, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Meta-toluic acid (4.0 g) was dissolved in tetrahydrofuran (98 mL). Thereto, 2M lithium diisopropylamide (59 mL) was added at room temperature, followed by stirring for 1 hour. Thereto, 1-bromo pentadecane (9.4 mL) was added, followed by stirring at room temperature for 21 hours. The reaction solution was poured to 1N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (3.7 g) having the following physical property values.

Workup

  1. stirringby stirring at room temperature for 21 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-63ec5d254b3c44518a87a15ae38bbf13
Source dataset
uspto-grants-2015_07
Patent number
US09085523B2

Reaction notes

Loading…