Methylparaben → HCID 19027292, compound

HRID 2256774Notes

Reaction equation

HRID 2256774 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1C=CC(C([O-])=O)=C[CH:9]=1.ClCCOCCO.[OH:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 19027304HCID 19027304, compound

Product 1

HCID 19027292HCID 19027292, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

These compounds were synthesized by a similar method. The representative synthesis of 4-(2-(2-hydroxyethoxy)ethoxy)benzoate (3) is presented. A solution of 2-(2-chloro ethoxy)ethanol 5.338 grams (0.04 mole) in 50 ml of acetonitrile was added dropwise to a solution of methyl 4-hydroxybenzoate 5.1 grams (0.036 mole) and 23.2 grams (0.168 mole) of powdered anhydrous potassium carbonate in 300 ml of acetonitrile at 80° C. After stirring the reaction mixture under reflux for 12 hours, 250 ml of the acetonitrile was then distilled and 250 ml dichloromethane was added. The reaction mixture was filtered through CELITE® and the solid was washed thoroughly with dichloromethane. Evaporation of the filtrate yielded product in the form of a yellow oil. Purification by flash chromatography on silica gel with 40% diethyl ether in dichloromethane yielded 7.1 g (87%). 1H-NMR (CDCl3, TMS): d=2.62 (s, 1H, --OH), 3.81-4.25 (m, 8H, --(OCH2CH2)2 --), 3.85 (s, 3H, --COOCH3), 6.9 and 7.9 (2d, 4 aromatic protons).

Workup

  1. customThese compounds were synthesized by a similar method
  2. temperatureunder reflux for 12 hours
  3. distillation250 ml of the acetonitrile was then distilled
  4. addition250 ml dichloromethane was added
  5. filtrationThe reaction mixture was filtered through CELITE®
  6. washthe solid was washed thoroughly with dichloromethane
  7. customEvaporation of the filtrate
  8. customyielded product in the form of a yellow oil
  9. customPurification by flash chromatography on silica gel with 40% diethyl ether in dichloromethane
  10. customyielded 7.1 g (87%)

Sources & evidence

ORD record
ord-a415f6657ec94900a85e4615e8660e6c
Source dataset
uspto-grants-1997_08
Patent number
US05656197

Reaction notes

Loading…