P-Cresol → Ethyl 2,2-bis(4-methylphenoxy)acetate

HRID 28114

Reaction equation

HRID 28114 reaction equation
[Na].[CH:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.Cl[CH:11](Cl)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C.C(OCC)C>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:11]([O:8][C:7]2[CH:2]=[CH:3][C:4]([CH3:9])=[CH:5][CH:6]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 2879P-CresolHCID 10808Ethyl dichloroacetateHCID 5360545Sodium

Product 1

HCID 23338923Ethyl 2,2-bis(4-methylphenoxy)acetateYield 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

Sodium (5.7 g) is dissolved in ethanol (160 cc), and a solution of para-cresol (27 g) in ethanol (20 cc) is added. The mixture is stirred for 1 hour at 20° C. and ethyl dichloroacetate (20 g) in solution in ethanol (20 cc) is then added. The mixture is heated under reflux for 20 hours and then allowed to cool. The white precipitate obtained is filtered off and the filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C. The oil thus obtained is taken up in diethyl ether (300 cc) and washed twice with N sodium hydroxide solution (100 cc each time) and twice with distilled water (100 cc each time). The ethereal phase is then dried over anhydrous sodium sulphate, filtered, and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methylphenoxy)acetate (29 g) is thus obtained as a yellow oil.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 20 hours
  3. temperatureto cool
  4. customThe white precipitate obtained
  5. filtrationis filtered off
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
  7. customThe oil thus obtained
  8. washwashed twice with N sodium hydroxide solution (100 cc each time) and twice with distilled water (100 cc each time)
  9. dry with materialThe ethereal phase is then dried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Sources & evidence

ORD record
ord-b1d0998d3cf545b793e561524dc0c9a6
Source dataset
uspto-grants-1980_09
Patent number
US04225589

Linked notes

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