Hydrochloric Acid → 4-(Hexadecyloxy)phenol

HRID 1728862Notes

Reaction equation

HRID 1728862 reaction equation
[H-].[Na+].[C:3]1([CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[OH:4].I[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl>CN(C)C=O.O1CCCC1>[CH2:27]([O:4][C:3]1[CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 110071-IodohexadecaneHCID 24758Sodium hydride

Product 1

HCID 43779374-(Hexadecyloxy)phenol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension, under argon, of 29 g of 60% sodium hydride in 350 ml of dimethylformamide is added dropwise over 40 minutes, 60.0 g of hydroquinone in 450 ml of dimethylformamide. The suspension is stirred at 0° C. for 1/2 hour; followed by the dropwise addition of 192 g of 1-iodohexadecane in 450 ml tetrahydrofuran. The reaction temperature is maintained at 0° C. during the addition of the alkyl halide; followed by stirring at room temperature for 3 hours. The mixture is poured carefully into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and concentrated in vacuo.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionextracted with chloroform
  3. washThe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a9a29a9aa6e4a3cb8ec4414e87cba81
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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