Hydrochloric Acid → 4-(Hexadecyloxy)phenol

HRID 1647600Notes

Reaction equation

HRID 1647600 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 suspension of 28.99 g of 60% sodium hydride in 350 ml of N,N-dimethylformamide, cooled to 0° C. and under argon is added 60 g of hydroquinone in 450 ml of N,N-dimethylformamide with stirring over 40 minutes. After an additional 30 minutes, 450 ml of tetrahydrofuran is added followed by 192 g of 1-iodohexadecane over one hour. The mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and evaporated to give the desired product as an oil.

Workup

  1. waitAfter an additional 30 minutes
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. extractionextracted with chloroform
  4. washThe organic layer is washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7daabf1825d542f195822f9a545b91f1
Source dataset
uspto-grants-1995_07
Patent number
US05432189

Reaction notes

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