Hydrochloric Acid → 4-[(Undec-10-en-1-yl)oxy]phenol

HRID 1250421Notes

Reaction equation

HRID 1250421 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[K+].[I-].[K+].C1(C)C=CC=CC=1S(O[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])(=O)=O.Cl>O.C(O)C.CO>[CH2:33]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=[CH2:23]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 86757726HCID 86757726, compound

Product 1

HCID 183260014-[(Undec-10-en-1-yl)oxy]phenol

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

FIG. 2 is a flow diagram showing the steps of synthesizing a representative monomer 1M according to the present invention. In a 50 ml of bi-neck bottle, 3.28 g of hydroquinone, 1.96 g of potassium hydroxide, 0.50 g of potassium iodide, 10.0 ml of methanol and 20.0 ml of ethanol are introduced and mixed. 3.00 g of 11-tolylsulfonyloxy-1-undecene is dropped slowly into the bottle and the resulting mixture is subsequently heated to the boiling point thereof. After the solvent is distillated off, 100.0 ml of cold water is added and 6N HCl is dropped until the mixture becomes acidic. Then the resulting mixture is subjected to extraction using ether. The organic layer is subjected to dehydration using magnesium sulfate, filtration, concentration and further purification with silica gel column chromatography, thereby obtaining a white solid product, 4-(10-undecenoxy)phenol.

Workup

  1. additionmixed
  2. temperaturethe resulting mixture is subsequently heated to the boiling point
  3. extractionThen the resulting mixture is subjected to extraction
  4. filtrationmagnesium sulfate, filtration, concentration and further purification with silica gel column chromatography

Sources & evidence

ORD record
ord-cc1f61d758544950b052aec9f432042e
Source dataset
uspto-grants-2002_01
Patent number
US06338902B1

Reaction notes

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