Homovanillic Acid → 4-(Acetyloxy)-3-methoxybenzeneacetic acid

HRID 2173335Notes

Reaction equation

HRID 2173335 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13].[CH3:14][C:15](OC(C)=O)=[O:16]>OP(O)(O)=O>[C:15]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13])(=[O:16])[CH3:14]

Participants

4

Reactant 2

HCID 1738Homovanillic AcidHCID 7918Acetic Anhydride

Product 1

HCID 2264844-(Acetyloxy)-3-methoxybenzeneacetic acid

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

A mixture of (4-hydroxy-3-methoxyphenyl)acetic acid (380 mg, 2.088 mmol) and H3PO4 (2 drops) in about 20 mL of Hac/Ac2O (v/v=1:1) was refluxed overnight, and then concentrated to dryness in vacuo. The residue was diluted with water (50 mL), and the result mixture was extracted with ethyl acetate (2*50 mL). The combined organic phase was washed with brine (100 mL) and dried over Na2SO4 and concentrated to give [4-(acetyloxy)-3-methoxyphenyl]acetic acid. 1H-NMR (400 MHz, CDCl3) δ ppm 6.97 (d, J=7.8 Hz, 1H), 6.84˜6.89 (m, 2H), 3.81 (s, 3H), 3.61 (s, 2H), 2.29 (s, 3H).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated to dryness in vacuo
  3. additionThe residue was diluted with water (50 mL)
  4. extractionthe result mixture was extracted with ethyl acetate (2*50 mL)
  5. washThe combined organic phase was washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9fdb577b8eac4aa093fc84ff105e97f1
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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