Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

HRID 1380087Notes

Reaction equation

HRID 1380087 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1.CO>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 1185343-Chloro-4-hydroxyphenylacetic acid

Product 1

HCID 92625Methyl 3-chloro-4-hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 67 g (0.38 moles) of 3-chloro-4-hydroxyphenylacetic acid, 1.5 g of p-toluenesulfonic acid, and 250 ml of methanol was refluxed overnight, i.e., about 18 hours. The excess methanol was removed by vacuum to give a thick tawny oil. This oil was dissolved in ether, twice washed with water, and dried over anhydrous sodium sulphate. The ethereal solution was filtered, the ether removed and a tawny oil remained. Using as solvent 2.5% v/v methanol in chloroform and a silica gel matrix, thin-layer chromotography showed that the oil was essentially homogeneous, there being only a trace impurity present at the origin, which is believed to be unreacted acid. This oil was satisfactory for use as the starting material for forming the ether of Example 1B.

Workup

  1. temperaturewas refluxed overnight
  2. customi.e., about 18 hours
  3. customThe excess methanol was removed by vacuum
  4. customto give a thick tawny oil
  5. washtwice washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationThe ethereal solution was filtered
  8. customthe ether removed
  9. customfor forming the ether of Example 1B

Sources & evidence

ORD record
ord-746d929fd5b14edc8a2513c9a6591580
Source dataset
uspto-grants-1986_04
Patent number
US04579866

Reaction notes

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