Benzyl chloroformate → Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

HRID 635159Notes

Reaction equation

HRID 635159 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.ClCCl>[C:23]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])([O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:24]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 199606-Amino-1-hexanol

Product 1

HCID 4184071Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

6-Aminohexan-1-ol (11.7 g, 100 mmol) and potassium carbonate (16.58 g, 120 mmol) were dissolved in 100 mL water and 70 mL dichloromethane. Benzylchloroformate (14.27 mL, 100 mmol) was added dropwise over 30 minutes at a temperature of 25-30° C. The resulting mixture stood overnight, then the dichloromethane layer was separated, washed with water (3×200 mL), 2 N HCl (3×50 mL) and finally with water (3×100 mL), dried, and evaporated to give a white solid. The solid was recrystallized in hexane-ethylacetate (8:2) to give a solid, which was collected and dried under vacuum at room temperature. Yield: 23 g (91%).

Workup

  1. customthe dichloromethane layer was separated
  2. washwashed with water (3×200 mL), 2 N HCl (3×50 mL) and finally with water (3×100 mL)
  3. customdried
  4. customevaporated
  5. customto give a white solid
  6. customThe solid was recrystallized in hexane-ethylacetate (8:2)
  7. customto give a solid, which
  8. customwas collected
  9. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-fb6736291cb04a9dba25d3dd66e388e5
Source dataset
uspto-grants-2001_02
Patent number
US06187762B1

Reaction notes

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