Dimethylformamide → Benzeneacetic acid, 4-(dodecyloxy)-

HRID 2165333Notes

Reaction equation

HRID 2165333 reaction equation
[CH3:1]N(C)C=O.CC[C:8]1[CH:13]=[C:12](O)[CH:11]=[CH:10][C:9]=1[O:15][C:16]([CH3:18])=O.C(Br)C[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[C:32](=[O:35])([O-])[O-:33].[K+].[K+]>O>[CH2:16]([O:15][C:9]1[CH:8]=[CH:13][C:12]([CH2:1][C:32]([OH:33])=[O:35])=[CH:11][CH:10]=1)[CH2:18][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 46173007HCID 46173007, compound

Product 1

HCID 10336152Benzeneacetic acid, 4-(dodecyloxy)-Yield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a dimethylformamide (DMF, 100 ml) solution of ethyl 4-hydroxyphenyl acetate (18 g, 0.1 mol.) and dodecyl bromide (25 g, 0.1 mol.) was added potassium carbonate (15 g, 0.1 mol.). The mixture was stirred at 100° C. for one hour. To the reaction solution, after cooling, was added water (200 ml), which was subjected to extraction with isopropyl ether (IPE). The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was dissolved in a mixture of methanol (100 ml) and tetrahydrofuran (THF, 100 ml). To the solution was added aqueous sodium hydroxide (10 g, 0.25 xol.), and the mixture was stirred at 50° C. The reaction solution was concentrated under reduced pressure, and the pH was adjusted to 4, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure to leave crude crystals Recrystallization from hexane-IPE gave 4-dodecyloxyphenylacetic acid (1-e, 20 g, 63%).

Workup

  1. temperatureTo the reaction solution, after cooling
  2. extractionwas subjected to extraction with isopropyl ether (IPE)
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe concentrate was dissolved in a mixture of methanol (100 ml) and tetrahydrofuran (THF, 100 ml)
  7. additionTo the solution was added aqueous sodium hydroxide (10 g, 0.25 xol.)
  8. stirringthe mixture was stirred at 50° C
  9. concentrationThe reaction solution was concentrated under reduced pressure
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer was washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. customto leave crude
  15. customcrystals Recrystallization from hexane-IPE

Sources & evidence

ORD record
ord-558d21888ece4ddfa2b6bc46ff6f12ce
Source dataset
uspto-grants-1990_07
Patent number
US04939274

Reaction notes

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