Potassium Carbonate → HCID 66906525, compound

HRID 1690475Notes

Reaction equation

HRID 1690475 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 66906525HCID 66906525, compoundYield 116.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.1 g, 5.2 mmol) in acetone (45 mL) and potassium carbonate (2.2 g, 15.7 mmol), was added 1-bromomethyl-4-methoxy-benzene (0.79 mL, 5.5 mmol). The mixture was refluxed for six hours. The solvent was evaporated in vacuo, and the residue was partitioned between water (50 mL) and ethyl acetate (80 mL). The organic layer was washed with water (2×50 mL), dried, concentrated in vacuo, and purified by flash column chromatography (Silica Gel, EtOAc/Hexane, 0% gradient to 100% 30 min) to give 3-(4-methoxy-benzyloxy)-phthalic acid dimethyl ester (2.0 g, 115% crude yield). The product was used in the next step without further purification.

Workup

  1. temperatureThe mixture was refluxed for six hours
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between water (50 mL) and ethyl acetate (80 mL)
  4. washThe organic layer was washed with water (2×50 mL)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. custompurified by flash column chromatography (Silica Gel, EtOAc/Hexane, 0% gradient to 100% 30 min)

Sources & evidence

ORD record
ord-bc08a7823aa4404695254699f6aa0634
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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