Boron trifluoride etherate → 1-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethan-1-one

HRID 1095267Notes

Reaction equation

HRID 1095267 reaction equation
B(F)(F)F.[CH3:5][CH2:6][O:7]CC.C([O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)(=O)C>C(O)(=O)C>[OH:13][C:14]1[C:15]([C:6](=[O:7])[CH3:5])=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 2762803,4,5-Trimethoxyphenyl acetate

Product 1

HCID 98993751-(6-Hydroxy-2,3,4-trimethoxyphenyl)ethan-1-oneYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Boron trifluride etherate (13.0 mL) was added dropwise to a solution of 3,4,5-tri-methoxyphenyl acetate 4 (6.78 g, 30 mmol) in glacial acetic acid (10 mL). The mixture was stirred at 70° C. for 2 h. Then the mixture was poured onto crushed ice (80 g). The light brown oil was separated and distilled under reduced pressure to furnish light yellow oil (5.56 g, 82%); 1H NMR (CDCl3, 200 M Hz) δ 13.42 (br s, 1H), 6.23 (s, 3H), 3.82 (s, 3H), 3.99 (s, 3H), 3.88 (s, 3H), 3.79 (s, 3H), 2.65 (s, 3H); 13C NMR (CDCl3, 50 M Hz) δ 203.3 (s), 161.8 (s), 160.0 (s), 155.2 (s), 134.7 (s), 108.4 (s), 96.0 (d), 60.9 (q, 2C), 56.0 (q), 31.8 (q).

Workup

  1. additionThen the mixture was poured
  2. customThe light brown oil was separated
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-29a9a94773bc42dcb127916bc3082d7e
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

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