Ammonia → 4-Hydroxymethyl-2,5-dimethylphenol

HRID 361973

Reaction equation

HRID 361973 reaction equation
[C:1]1([OH:9])[C:2]([CH3:8])=[CH:3][CH:4]=[C:5]([CH3:7])[CH:6]=1.[OH-:10].[Na+].[CH2:12]=O.N>C(O)(=O)C.O>[OH:10][CH2:12][C:4]1[C:5]([CH3:7])=[CH:6][C:1]([OH:9])=[C:2]([CH3:8])[CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 72672,5-DimethylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 109426404-Hydroxymethyl-2,5-dimethylphenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
12 °C

Procedure

Into a 5 liter four-necked flask were charged 610.9 g of 2,5-xylenol, 200 gof sodium hydroxide and 2500 g of water. While stirring at 12° C., 565 g of 37% formaldehyde was added dropwise thereto over 1 hour and 30 minutes, and the reaction was conducted for 4 more hours. After completionof the reaction, 89 g of 28% aqueous ammonia solution was added and the mixture was stirred for 30 minutes. Thereafter, 400 g of acetic acid was added thereto, and the resulting mixture was filtered and washed with water. The filtered product thus obtained was dried to obtain 609 g of 4-hydroxymethyl-2,5-dimethylphenol. Purity measured by liquid chromatography (LC): 99%

Workup

  1. custom30 minutes
  2. additionwas added
  3. stirringthe mixture was stirred for 30 minutes
  4. filtrationthe resulting mixture was filtered
  5. washwashed with water
  6. customThe filtered product thus obtained
  7. customwas dried

Sources & evidence

ORD record
ord-78fd208b70014bb693819b515af4127a
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Linked notes

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