Benzyl Alcohol → Benzyl phenyl carbonate

HRID 538896Notes

Reaction equation

HRID 538896 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11].O.OS(O)(=O)=O>C(Cl)Cl>[C:10](=[O:11])([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 1118Sulfuric AcidHCID 15891Phenyl chloroformate

Product 1

HCID 11183772Benzyl phenyl carbonateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl alcohol (10.8 g, 100.0 mol) was dissolved in 100 mL of CH2Cl2. The solution was cooled down to 0° C. and phenyl chloroformate (15.7 g, 100 mol) was slowly added dropwise. The solution was stirred at RT overnight. Addition of 100 mL of H2O was followed by 2× washes with 100 mL of 2M H2SO4 each time. The organic phase was separated off and dried over Na2SO4. The solvent was removed in vacuo to obtain a colorless liquid (22.5 g, 99%).

Workup

  1. customThe organic phase was separated off
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4d93e95d433242799749fe36f4d3c69d
Source dataset
uspto-grants-2014_10
Patent number
US08865863B2

Reaction notes

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