4-Hydroxybenzyl Alcohol → Methyl-phenyl-carbamic Acid 4-hydroxymethyl-phenyl Ester

HRID 1831424Notes

Reaction equation

HRID 1831424 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH3:10][N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12](Cl)=[O:13]>C(Cl)Cl>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:12](=[O:13])[N:11]([CH3:10])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1254-Hydroxybenzyl AlcoholHCID 77969Carbamic chloride, N-methyl-N-phenyl-

Product 1

HCID 69518671Methyl-phenyl-carbamic Acid 4-hydroxymethyl-phenyl EsterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-hydroxymethylphenol (10 mmol) and 4-diazabicyclo[2.2.2]octane (DABCO) (10 mmol) in CH2Cl2 (30 mL) was added N-methyl-N-phenylcarbamoyl chloride (10 mmol). The reaction mixture was stirred for 16 hours at rt, added CH2Cl2 (20 mL) and washed with 1M aqueous HCl and brine. The organic phase was dried (MgSO4) and evaporated to give the crude product which was purified by FC (Quad flash 40 EtOAc-Heptane 1:1) to give 2.18 g (85%) of the title compound as an oil.

Workup

  1. washwashed with 1M aqueous HCl and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customto give the crude product which
  5. customwas purified by FC (Quad flash 40 EtOAc-Heptane 1:1)

Sources & evidence

ORD record
ord-f76f50c75cbc4fb79862e077f70730da
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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