Formaldehyde → HCID 69677328, compound
Reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9].C=O>C(O)(=O)C>[CH2:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9].[CH2:1]=[O:7].[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A one liter flask was charged with 301.2 g phenol (3.2 moles) and 194 g. N-ethylaniline (1.6 moles). The reaction mixture was heated to 70° C. and then 192 g 50% formalin (3.2 moles) was added over 45 minutes at 70-72° C. After 1½ hours at 71-73° C., 4 g acetic acid was added. The temperature was raised to 80° C. and maintained at 80° C. for 2 hours. The temperature was raised to 100° C. and maintained for 1½ hour. Reaction mixture was then atmospherically distilled to 160° C. to collect 156 g distillate. Phenol (92.1 g) was then recovered by vacuum distillation increasing temperature to 190° C. while increasing vacuum to 30 inches of mercury. Product yield was 432.7 g and is characterized in Table 1B.
Workup
- waitAfter 1½ hours at 71-73° C.
- temperatureThe temperature was raised to 80° C.
- temperaturemaintained at 80° C. for 2 hours
- temperatureThe temperature was raised to 100° C.
- temperaturemaintained for 1½ hour
- customReaction mixture
- distillationwas then atmospherically distilled to 160° C.
- distillationto collect 156 g distillate
- distillationPhenol (92.1 g) was then recovered by vacuum distillation
- temperatureincreasing temperature to 190° C.
- temperaturewhile increasing vacuum to 30 inches of mercury
Sources & evidence
- ORD record
- ord-b140777f7ecf40f2bc7a4403d4b7910f
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06780511B2
Reaction notes
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