Water → HCID 21470408, compound

HRID 2294750Notes

Reaction equation

HRID 2294750 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])(=O)=O)=CC=1.O[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1.[H-].[Na+].[OH2:39]>C(O)CCC>[CH2:21]([O:36][C:33]1[CH:34]=[CH:35][C:30]([C:27]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)=[C:31]([OH:39])[CH:32]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]

Participants

6

Reactant 4

HCID 962WaterHCID 71124,4'-DihydroxybiphenylHCID 24758Sodium hydrideHCID 11141895HCID 11141895, compound

Product 1

HCID 21470408HCID 21470408, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent3×

Conditions

Temperature
110 °C

Procedure

The above-prepared 2.60 g (8.02 mM) of 10-undecenyl p-toluenesulfonate, 3.0 g (16.0 mM) of dihydroxybiphenyl and 3 ml of butanol were mixed and sufficiently stirred. To the mixture, a solution of 0.41 g (9.74 mM) of sodium hydride in 6 ml of butanol was added, followed by heat-refluxing for 7 hours at 110° C. After the reaction, the reaction mixture was subjected to distilling-off of butanol and addition of water, followed by extraction with ether to obtain an extract. The extract was dried with anhydrous sodium sulfate, followed by distilling-off of ether and purification by column chromatography (eluent: methylene chloride) to obtain 1.55 g (3.82 mM) of p-(10-undecenyl)oxyhydroxybiphenyl (Yield: 47.6%).

Workup

  1. customAfter the reaction
  2. extractionfollowed by extraction with ether
  3. customto obtain an extract
  4. dry with materialThe extract was dried with anhydrous sodium sulfate
  5. distillationfollowed by distilling-off of ether and purification by column chromatography (eluent: methylene chloride)

Sources & evidence

ORD record
ord-7427014f914c414fb694d6456fac1cd8
Source dataset
uspto-grants-1997_11
Patent number
US05690858

Reaction notes

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