Sulfuric Acid → Methyl 4-hydroxy-3-methoxyphenylacetate

HRID 2427926Notes

Reaction equation

HRID 2427926 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.S(=O)(=O)(O)O.[C:19](=O)(O)[O-].[Na+]>CO>[OH:9][C:8]1[CH:10]=[CH:11][C:3]([CH2:2][C:1]([O:13][CH3:19])=[O:12])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1738Homovanillic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 85214Methyl 4-hydroxy-3-methoxyphenylacetateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of homovanillic acid 10 (2 g, 11 mmol) and sulfuric acid (500 ml, 9.4 mmol) in methanol (100 ml) was refluxed for 3 hours. After cooling, a sodium bicarbonate solution was added to the reaction mixture. The product was extracted with CH2Cl2 (2×50 ml). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure to give methyl 4-hydroxy-3-methoxyphenylacetate 9 (2 g, 94%) in the form of a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.00-6.70 (m, 3H), 5.82 (br s, OH), 3.87 (s, 3H), 3.70 (s, 3H), 3.56 (s, 2H). 13C NMR (CDCl3, 75 MHz) δ 172.6, 146.6, 144.8, 125.7, 122.1, 114.5, 111.8, 55.9, 52.1, 40.8.

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted with CH2Cl2 (2×50 ml)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3eae02a943f44559879a174ed5d9d2f2
Source dataset
uspto-grants-2011_06
Patent number
US07968735B2

Reaction notes

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