Formaldehyde → HCID 69677332, compound

HRID 1836935Notes

Reaction equation

HRID 1836935 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:1]=[O:7].[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 712Formaldehyde2×HCID 996PhenolHCID 7515N-Methylaniline2×

Product 1

HCID 69677332HCID 69677332, compound

Conditions

Temperature
60 °C

Procedure

A one liter flask was charged with 244.7 g phenol (2.6 moles) and 86.1 g 50% formalin (1.44 moles). The reaction mixture was heated to 60° C. and then 85.8 g N-methylaniline (0.8 mole) and added over 30 minutes at 60° C. The temperature was lowered to 50° C. and 86.1 g 50% formalin (1.44 moles) quickly added. The temperature was raised to 55° C. and than 85.7 g N-methylaniline (0.8 mol) added over 32 minutes at 55-60° C. After 20 minutes at 60° C. the temperature raised to 100° C. and maintained at 100° C. for one hour. Reaction mixture was then atmospherically distilled to 160° C. to collect 136.8 g distillate. Phenol (56.3 g) was then recovered by vacuum distillation increasing temperature to 190° C. while increasing vacuum to 30 inches of mercury. Vacuum was broken and 100 ml deionized water added over 40 minutes at about 190° C. Vacuum was then applied to remove water at 190° C. under 30 inches of mercury. Product yield was 372 g and is characterized in Table 3B and Table 5.

Workup

  1. customwas lowered to 50° C.
  2. additionadded over 32 minutes at 55-60° C
  3. temperatureAfter 20 minutes at 60° C. the temperature raised to 100° C.
  4. temperaturemaintained at 100° C. for one hour
  5. customReaction mixture
  6. distillationwas then atmospherically distilled to 160° C.
  7. distillationto collect 136.8 g distillate
  8. distillationPhenol (56.3 g) was then recovered by vacuum distillation
  9. temperatureincreasing temperature to 190° C.
  10. temperaturewhile increasing vacuum to 30 inches of mercury
  11. additionadded over 40 minutes at about 190° C
  12. customto remove water at 190° C. under 30 inches of mercury

Sources & evidence

ORD record
ord-649e2aee0c8848298f74da3a4dfab1e1
Source dataset
uspto-grants-2004_08
Patent number
US06780511B2

Reaction notes

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