Toluene → p-Tolyl-carbamic acid 2-isopropyl-cyclohexyl ester

HRID 1472239Notes

Reaction equation

HRID 1472239 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[CH:18]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[OH:27])([CH3:20])[CH3:19]>O>[CH:18]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:27][C:8](=[O:9])[NH:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 1140TolueneHCID 693254-Methylphenyl isocyanateHCID 953312-Isopropylcyclohexan-1-ol

Product 1

HCID 46898912p-Tolyl-carbamic acid 2-isopropyl-cyclohexyl esterYield 56.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

75.6 g (0.56 mol) of para-tolylisocyanate were placed with 500 ml toluene in a one liter vessel and subsequently 73.4 g (0.51 mol) of 2-isopropylcyclohexanol were added. The reaction mixture was heated to reflux for 6 hours. After cooling to room temperature 50 g of water were added and the mixture was refluxed for one more hour. After phase separation the solvent was stripped off and the crude product recrystallized from 235 g of n-heptane. The product (79.8 g) was obtained in form of off-white crystals in 99.2% purity. This corresponds to a theoretical yield of 56%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. additionwere added
  4. temperaturethe mixture was refluxed for one more hour
  5. customAfter phase separation the solvent
  6. customthe crude product recrystallized from 235 g of n-heptane

Sources & evidence

ORD record
ord-e6d34293247c47c892eda84ded0eb262
Source dataset
uspto-grants-2015_04
Patent number
US09012497B2

Reaction notes

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