Potassium Carbonate → HCID 22714151, compound

HRID 896071Notes

Reaction equation

HRID 896071 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 22714151HCID 22714151, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl-3-hydroxybenzoate (5.0 g, 32.8 mmol) in acetone (30 mL) was added potassium carbonate (6.82 g, 49.2 mmol) and p-methoxybenzyl chloride (4.5 mL, 32.8 mmol). The contents are heated under reflux for forty eight hours, concentrated under pressure and partitioned between ethyl acetate (100 mL) and water (100 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield the title compound (8.87 g, 99%). 1H NMR (CDCl3): □ 7.8 (m, 2H), 7.4 (m, 3H), 7.15 (m, 1H), 6.9 (d, 2H), 5.1 (s, 2H), 3.9 (s, 3H), 3.8 (s, 3H).

Workup

  1. temperatureThe contents are heated
  2. temperatureunder reflux for forty eight hours
  3. concentrationconcentrated under pressure
  4. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d024d8e7c9b94822bf7e5d284ce169a5
Source dataset
uspto-grants-2005_07
Patent number
US06919335B2

Reaction notes

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