Acetic Anhydride → Acetoxy-(4-methoxy-phenyl)-acetic acid

HRID 1272066Notes

Reaction equation

HRID 1272066 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]([OH:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].CCN(CC)CC>C1COCC1>[C:14]([O:11][CH:7]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1120564-Methoxymandelic acid

Product 1

HCID 18456650Acetoxy-(4-methoxy-phenyl)-acetic acidYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methoxymandelic acid (5.00 g, 27.44 mmol) was dissolved in 100 mL of THF. To this solution was added acetic anhydride (2.85 mL, 30.18 mmol), followed by Et3N (10 mL). The resulting mixture was stirred at room temperature overnight, concentrated, re-suspended in water, and extracted with EtOAc. The combined organic phase was dried over Na2SO4, and concentrated to give 5.95 g yellow syrup as the intermediate 79a. 1H NMR (300 MHz, CDCl3) δ 7.38 (d, 2H, J=8.67 Hz), 6.90 (d, 2H, J=8.67 Hz), 5.87 (s, 1H), 3.80 (s, 3H), 2.16 (s, 3H). LCMS (ESI−) [M−H]/z Calc'd 223, found 223.

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c2e80a004ee54e5bbf0973a2c0752f42
Source dataset
uspto-grants-2007_04
Patent number
US07208500B2

Reaction notes

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