Phenol → Phenyl 2-hydroxy-4,5-dimethoxybenzoate

HRID 1621068Notes

Reaction equation

HRID 1621068 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15]1(O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O=S(Cl)Cl>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([O:6][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:5]

Participants

5

Reactant 3

HCID 996PhenolHCID 24386Thionyl Chloride2×HCID 115646502-Hydroxy-4,5-dimethoxybenzoic acid

Product 1

HCID 53424183Phenyl 2-hydroxy-4,5-dimethoxybenzoateYield 64%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 10 g of xylene were suspended 1.0 g of compound (2a) and 522 mg of phenol, to which 460 μL of SOCl2 was then added dropwise before heating to reflux for 3 hours, followed by further adding 184 μL of SOCl2 and additionally heating to reflux for one hour. The reaction solvent was distilled off, followed by adding methanol to the residue before stirring. The precipitated crystal was collected by filtration to provide 880 mg of phenyl 2-hydroxy-4,5-dimethoxybenzoate (3a) at a yield of 64%.

Workup

  1. temperaturebefore heating
  2. temperatureto reflux for 3 hours
  3. temperatureadditionally heating
  4. temperatureto reflux for one hour
  5. distillationThe reaction solvent was distilled off
  6. additionby adding methanol to the residue
  7. filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-473cce09e62d432a9c8e436c2fb8e2f4
Source dataset
uspto-grants-2014_07
Patent number
US08772528B2

Reaction notes

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