Benzyl Alcohol → Benzyl carbamate

HRID 1578300Notes

Reaction equation

HRID 1578300 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C[O:12][C:13]([N:15]=C=O)=O>C(Cl)Cl>[C:13](=[O:12])([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH2:15]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 12767988HCID 12767988, compound

Product 1

HCID 12136Benzyl carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl carbamate is prepared by dissolving 354 mg. (3.28 mmoles) benzyl alcohol in 3 ml. methylene chloride in a 2-neck 10 ml. flask fitted with a condenser topped with a drying tube and serum cap. The solution is cooled in an ice bath and 0.48 ml. (770 mg., 3.5 mmoles) of trichloroethoxycarbonyl isocyanate is introduced with a syringe through the serum cap. An exotherm is noted. After stirring at room temperature for 40 minutes, the solution is concentrated to an oil and recrystallized from cyclohexane to yield 980 mg. of benzyl 2,2,2-trichloroethyl imidodicarboxylate, m.p. 88.5°-89.5° C. An analytical sample has a m.p. 89.5°-90.5° C.

Workup

  1. dissolutionby dissolving 354 mg
  2. customflask fitted with a condenser
  3. customtopped with a drying tube
  4. customserum cap
  5. temperatureThe solution is cooled in an ice bath
  6. customcap
  7. concentrationthe solution is concentrated to an oil
  8. customrecrystallized from cyclohexane
  9. customto yield 980 mg

Sources & evidence

ORD record
ord-7519c02b460a4438bc209852b6e81913
Source dataset
uspto-grants-1981_09
Patent number
US04292427

Reaction notes

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