Formaldehyde → 4397-13-1

HRID 1904053Notes

Reaction equation

HRID 1904053 reaction equation
[CH2:1]=[O:2].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[OH:11].[OH-].[Na+]>O>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:1][OH:2])[C:5]=1[OH:11]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 77712,4-DimethylphenolHCID 14798Sodium Hydroxide2×

Product 1

HCID 114805504397-13-1

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 38% solution of formaldehyde (32.0 grams, 0.4 mol) was added to a stirred solution of 2,4-dimethylphenol (36.6 grams, 0.3 mol) in water (100 ml) containing sodium hydroxide (14 gr., 0.35 mol) and heated at 50° C. for 4 to 5 hours. The reaction was cooled and solid sodium hydroxide added to precipitate the salt of the product. The solid was removed by filtration and dissolved in water. This solution was neutralized with carbon dioxide (dry ice) and the resulting mixture was extracted with methylene chloride. The organic layer was removed, dried, and evaporated to yield a light brown solid. This solid was washed in hexane containing a small amount of toluene to afford a tan solid. The NMR1 and FD/MS2 data support the structure

Workup

  1. temperatureThe reaction was cooled
  2. customto precipitate the salt of the product
  3. customThe solid was removed by filtration
  4. dissolutiondissolved in water
  5. extractionthe resulting mixture was extracted with methylene chloride
  6. customThe organic layer was removed
  7. customdried
  8. customevaporated
  9. customto yield a light brown solid
  10. washThis solid was washed in hexane containing a small amount of toluene
  11. customto afford a tan solid

Sources & evidence

ORD record
ord-b8f50652eca54af689b169939b215f81
Source dataset
uspto-grants-1984_03
Patent number
US04439564

Reaction notes

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