Acetic Anhydride → Methyl 4-acetoxy-3-allylbenzoate

HRID 2421825Notes

Reaction equation

HRID 2421825 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[OH:21])[C:14]([O:16][CH3:17])=[O:15])[CH:9]=[CH2:10]>N1C=CC=CC=1>[C:1]([O:21][C:20]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 939882Methyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 67094163Methyl 4-acetoxy-3-allylbenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (200 μL, 218 mg, 2.13 mmol) was added dropwise to a solution of phenol 5 (315 mg, 1.64 mmol) in pyridine (1.5 mL) at room temperature. The mixture was stirred for 14 hours before the solvent was removed. The residue was purified by chromatography (10:1, hexanes:EtOAc) to afford 6 (337 mg, 88%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.95-7.90 (m, 2H), 7.11 (d, J=8.2 Hz, 1H), 5.92-5.83 (m, 1H), 5.12-5.03 (m, 2H), 3.88 (s, 3H), 3.33 (d, J=6.5 Hz, 2H), 2.29 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 169.2, 166.8, 153.0, 135.6, 132.7, 132.4, 129.4, 128.4, 123.0, 117.2, 52.6, 35.0, 21.3; IR (neat) νmax 3080, 3005, 2980, 2953, 2916, 2845, 1765, 1722, 1639, 1609, 1589, 1493, 1437, 1418, 1369, 1285, 1263, 1190, 1163, 1121 cm−1; HRMS (ESI+) m/z 235.1076 (M+H+, C13H15O4 requires m/z 235.0970).

Workup

  1. customwas removed
  2. customThe residue was purified by chromatography (10:1, hexanes:EtOAc)

Sources & evidence

ORD record
ord-0bec2cca8c6945479440425c09c36d1a
Source dataset
uspto-grants-2011_06
Patent number
US07960353B2

Reaction notes

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