Phenol → Benzene, (hexadecyloxy)-

HRID 327855

Reaction equation

HRID 327855 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[K+].C1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:18]1([O:24][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 1140TolueneHCID 82131-BromohexadecaneHCID 14797Potassium Hydroxide

Product 1

HCID 4438129Benzene, (hexadecyloxy)-Yield 98%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
92 °C

Procedure

A 1-liter three necked round bottom flask was charged with 100 grams (0.33 moles) of 1-bromohexadecane, 92.5 grams (0.99 moles) of phenol, 55.2 grams (0.99 moles) of potassium hydroxide, 10 grams of tetra-n-butylammonium bromide, 167 ml of toluene, and 167 ml of water. The flask was fitted with a mechanical stirrer, nitrogen inlet, condenser, thermometer and heating mantle. The reaction mixture was heated to reflux at about 92° C., under a nitrogen purge for 16 hours with constant agitation. After 16 hours, the mixture was cooled and transferred to a separatory funnel where the aqueous layer was removed and the upper toluene layer was washed three times with 200 ml 0.5N NAOH and three times with 200 ml deionized water. The toluene was removed under reduced pressure leaving 102.6 grams (98% yield) of n-hexadecyl phenyl ether. Analysis by gas chromatography showed that the product was 98.3% pure.

Workup

  1. customThe flask was fitted with a mechanical stirrer, nitrogen inlet, condenser
  2. temperaturethermometer and heating mantle
  3. temperatureThe reaction mixture was heated
  4. custompurge for 16 hours with constant agitation
  5. temperaturethe mixture was cooled
  6. customtransferred to a separatory funnel
  7. customwhere the aqueous layer was removed
  8. washthe upper toluene layer was washed three times with 200 ml 0.5N NAOH and three times with 200 ml
  9. customThe toluene was removed under reduced pressure

Sources & evidence

ORD record
ord-bf66e1cdae314981bd734c887691cbc3
Source dataset
uspto-grants-1993_12
Patent number
US05274148

Linked notes

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