Benzoyl chloride → Phenol

HRID 1472945Notes

Reaction equation

HRID 1472945 reaction equation
C(Cl)(=[O:8])C1C=CC=CC=1.[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O>[CH3:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10].[C:21]1([OH:8])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 8182Dodecane

Product 2

HCID 996PhenolYield 27,290.4%HCID 8182Dodecane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

4,4′-methylene diphenyl dicarbamate (38 g, 86.8 mmole) and inhibitor benzoyl chloride (0.09 g, 0.6 mmole) were charged to 500 ml three-neck bottle with solvent dodecane (250 ml, 188.12 g). The mixture was stirred with a magnetic stirbar and heated to 210° C. with an oil bath. One neck of the bottle was equipped with a thermometer and charged with nitrogen, and another neck was connected to a divide tube which was further connected to a condenser to charge with cold water. The upper end of the condenser was connected to a grease seal. The reaction was carried out for 2.5 hours. The progress of the reaction was monitored by FT-IR. It was observed that the absorption peak at 1720 cm−1 and the absorption peak at 3335 cm−1 disappeared completely, and the absorption peak appeared at 2270 cm−1. After part of n-dodecane (100 ml) and produced phenol (15.41 g) was retrieved from the divide tube, the heating was stopped and the reaction ended.

Workup

  1. customOne neck of the bottle was equipped with a thermometer
  2. additioncharged with nitrogen, and another neck
  3. customwas connected to a divide tube
  4. customwhich was further connected to a condenser
  5. customseal

Sources & evidence

ORD record
ord-2abd3d4751604022b6de1771a9c3d3dc
Source dataset
uspto-grants-2015_04
Patent number
US09012676B2

Reaction notes

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