1-Bromododecane → Benzeneacetic acid, 4-(dodecyloxy)-

HRID 1650808Notes

Reaction equation

HRID 1650808 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.CN(C)C=O>[CH2:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

7

Reactant 4

HCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a dimethylformamide (DMF, 100 ml) solution of ethyl 4-hydroxyphenylacetate (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) and the mixture 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 mol.), and the mixture was stirred at 50° C. The reaction solution was concentrated under reduced pressure, whose 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. extractionthe mixture was 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. stirringthe mixture was stirred at 50° C
  8. concentrationThe reaction solution was concentrated under reduced pressure, whose pH
  9. extractionfollowed by extraction with ethyl acetate
  10. washThe organic layer was washed with water
  11. customdried
  12. concentrationconcentrated under reduced pressure
  13. customto leave crude crystals
  14. customRecrystallization from hexane-IPE

Sources & evidence

ORD record
ord-16aebde31c074e54a8d11bff05acfb7c
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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