Tyrosol → Methyl-phenyl-carbamic Acid 4-(2-hydroxy-ethyl)-phenyl Ester

HRID 1831425Notes

Reaction equation

HRID 1831425 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:11][N:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](Cl)=[O:14]>C(Cl)Cl>[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:13](=[O:14])[N:12]([CH3:11])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 10393TyrosolHCID 77969Carbamic chloride, N-methyl-N-phenyl-

Product 1

HCID 69520342Methyl-phenyl-carbamic Acid 4-(2-hydroxy-ethyl)-phenyl EsterYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-Hydroxyethyl)phenol (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 2.69 g (99%) of the title compound as crystals.

Workup

  1. washwashed with 1M aqueous HCl and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-3c3aa17a022a4ad5bfcf6a892c9e8e30
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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