Acetic Anhydride → 3-Acetoxy-5-benzyloxybenzoic acid

HRID 1713299Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(O)(=O)C>[C:19]([O:18][C:16]1[CH:15]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:17]=1)[C:12]([OH:14])=[O:13])(=[O:21])[CH3:20]

Participants

Conditions

Temperature: 120 °C

Procedure

3-Benzyloxy-5-hydroxybenzoic acid (2.16 g) and acetic anhydride (15 mL) were suspended in acetic acid (15 mL), and the resulting mixture was stirred at 120° C. for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/1 to 1/0) to give the title compound (1.74 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue obtained
customwas purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/1 to 1/0)

Sources & evidence

ORD record: ord-2b059118e70d4af8a7e9ef26f4064e66
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795236B2

Reaction notes

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