Hydrochloric Acid → HCID 19036688, compound

HRID 264349Notes

Reaction equation

HRID 264349 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22]Br)[CH3:20].Cl>CN(C)C=O>[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22][O:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=1)[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 868042-Ethylhexyl bromide

Product 1

HCID 19036688HCID 19036688, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 30 ml of dimethylformamide (DMF) were added 5.00 g (29.9 mmol) of methyl 2,4-dihydroxybenzoate and 4.52 g (32.7 mmol) of potassium carbonate, and 6.32 g (32.7 mmol) of 2-ethylhexyl bromide was added thereto dropwise at room temperature. After the dropwise addition, the mixture was stirred at 80° C. for 5.5 hours. The reaction mixture was added to 200 ml of dilute hydrochloric acid and extracted with a 150 ml portion and two 50 ml portions of ethyl acetate. The resulting extract was washed successively with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product. The resultant crude product was purified by column chromatography to obtain 5.89 g (yield: 78%) of methyl 4-(2-ethylhexyloxy)-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 1) as a colorless, clear and oily substance. The analytical results of the product are shown below. ##STR22##

Workup

  1. additionwas added
  2. customdropwise at room temperature
  3. additionAfter the dropwise addition
  4. extractionextracted with a 150 ml portion and two 50 ml portions of ethyl acetate
  5. extractionThe resulting extract
  6. washwas washed successively with water
  7. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto obtain a crude product
  10. customThe resultant crude product was purified by column chromatography

Sources & evidence

ORD record
ord-80f75d592cbc471ca4fec0cd814319cc
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Reaction notes

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