2,5-Dimethylphenol → HCID 23451686, compound

HRID 1278454Notes

Reaction equation

HRID 1278454 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[OH-].[Na+].C([O-])(=O)C.[Na+].[C:17](=[C:20]([CH2:23][CH2:24]Cl)[CH2:21]Cl)([CH3:19])[CH3:18]>O>[C:17](=[C:20]1[CH2:23][CH2:24][C:6]2([CH:7]=[C:2]([CH3:1])[C:3](=[O:9])[CH:4]=[C:5]2[CH3:8])[CH2:21]1)([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 72672,5-DimethylphenolHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 23451717HCID 23451717, compound

Product 1

HCID 23451686HCID 23451686, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

2,5-Dimethylphenol (9.7 g, 0.08 mol) was added to a solution of sodium hydroxide (3.2 g, 0.08 mol) and sodium acetate (3.3 g, 0.04 mol) in distilled water (50 mL). The mixture was cooled to 15° C. and 2-isopropylidene-1,4-dichlorobutane (15 g, 0.09 mol) was added over 1 hour under nitrogen. After stirring at room temperature for 6 hours, the reaction mixture was extracted with ether. The ether extracts were washed with 10% sodium hydroxide, water, and dried (Na2SO4). Concentration gave 18.5 g of crude material consisting of mainly the alkylated phenol having the structure: ##STR38## A sample purified by column chromatography (silica gel) had the following spectral characteristics:

Workup

  1. extractionthe reaction mixture was extracted with ether
  2. washThe ether extracts were washed with 10% sodium hydroxide, water
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-ad46fa942fca4bf397edcbf01a177524
Source dataset
uspto-grants-1981_07
Patent number
US04281204

Reaction notes

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