Methanol → Methyl (2-hydroxyphenyl)acetate

HRID 2309571Notes

Reaction equation

HRID 2309571 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:17])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

HCID 89719Methyl (2-hydroxyphenyl)acetate

Conditions

Temperature
-20 °C

Procedure

250 g of 2-hydroxy-benzeneacetic acid are boiled for 24 hours with 2 1 of methanol and 75 ml of sulfuric acid, d 1.84. The solution is poured onto ice water and extracted with chloroform. The chloroform solution is shaken against a solution of sodium hydrogen carbonate and water and is then dried with magnesium sulfate. The solution is evaporated, the residue being dissoved in methylene chloride and treated with active carbon. 400 ml of petroleum ether are added to the solution with gentle heating. The solution is cooled to -20° C. whereupon the crystals are filtered off and washed with petroleum ether.

Workup

  1. additionThe solution is poured onto ice water
  2. extractionextracted with chloroform
  3. dry with materialis then dried with magnesium sulfate
  4. customThe solution is evaporated
  5. additiontreated with active carbon
  6. addition400 ml of petroleum ether are added to the solution with gentle heating
  7. filtrationare filtered off
  8. washwashed with petroleum ether

Sources & evidence

ORD record
ord-59c8e1a7dc6a4642bfbd2f1dab88da46
Source dataset
uspto-grants-1987_09
Patent number
US04695648

Reaction notes

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