Formaldehyde → HCID 69677332, compound

HRID 1836934Notes

Reaction equation

HRID 1836934 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C=O>C(O)=O>[CH3:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:1]=[O:7].[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 996Phenol4×HCID 7515N-Methylaniline

Product 1

HCID 69677332HCID 69677332, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A one liter flask was charged with 376.4 g phenol (4.0 moles), 171.5 g N-methylaniline (1.6 moles) and 7.0 g 90% formic acid. The reaction mixture was heated to 70° C. and then 191 g 50% formalin (3.2 moles) was added at 70° C. over 1 hour. The temperature was maintained at 70° C. for 2 hours at which time the percent free phenol was determined to be 34.8% (vs. 50.5% for no reaction of phenol). The temperature was raised to 100° C. and maintained at 100° C. for one hour at which time the percent free phenol was 33.6%. Reaction mixture was then atmospherically distilled to 160° C. to collect 163 g distillate. Phenol (170 g) was then recovered by vacuum distillation increasing temperature to 190° C. while increasing vacuum to 30 inches of mercury. Product yield was 397 g and is characterized in Table 2B and Table 5.

Workup

  1. temperatureThe temperature was raised to 100° C.
  2. customReaction mixture
  3. distillationwas then atmospherically distilled to 160° C.
  4. distillationto collect 163 g distillate
  5. distillationPhenol (170 g) was then recovered by vacuum distillation
  6. temperatureincreasing temperature to 190° C.
  7. temperaturewhile increasing vacuum to 30 inches of mercury

Sources & evidence

ORD record
ord-b8984441de0c42ca82c7e84525b1d6e3
Source dataset
uspto-grants-2004_08
Patent number
US06780511B2

Reaction notes

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