Dimethylformamide → HCID 69130305, compound

HRID 264356

Reaction equation

HRID 264356 reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)/[CH:25]=[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])\[CH3:27]>O>[CH3:27]/[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])=[CH:25]\[CH2:24][O:17][C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:6])[CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Product 1

HCID 69130305HCID 69130305, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 80 m of DMF were poured 13.1 g (78.0 mmol) of methyl 2,4-dihydroxybenzoate and 18.9 g (86.9 mmol) of potassium carbonate, and 12.0 g (86.9 mmol) of geranyl bromide was added thereto dropwise at 5° C. After the addition, the mixture was stirred at room temperature for 1 hour, poured into 300 ml of water, and extracted with 250 ml of ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The resulting crude product was purified by column chromatography to obtain 18.1 g (yield: 75%) of methyl 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 31) as a colorless, clear and oily substance. The analytical results are shown below. ##STR52##

Workup

  1. additionwas added
  2. customdropwise at 5° C
  3. additionAfter the addition
  4. extractionextracted with 250 ml of ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ed26f7e8ce11468380f41976500fe5b4
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Linked notes

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