Trimethyl orthoformate → Methyl 3-Hydroxyphenylacetate

HRID 384127Notes

Reaction equation

HRID 384127 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O-:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12]OC(OC)OC>CO>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 6950813HCID 6950813, compound

Product 1

HCID 39129Methyl 3-Hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-hydroxyphenylacetate (2.0 g) in methanol (10 ml), 250 mg of tosic acid monohydrate and 2.9 ml of trimethoxymethane were added, and the reaction solution was heated to reflux for 5 hours. The reaction solution was cooled, and then the solvent was distilled off under reduced pressure. The residual residue was diluted with diethyl ether, washed with a saturated aqueous sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-50:50)) to afford the title compound as a colorless oil.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for 5 hours
  3. temperatureThe reaction solution was cooled
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe residual residue was diluted with diethyl ether
  6. washwashed with a saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue obtained
  10. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-50:50))

Sources & evidence

ORD record
ord-0852e8820a14436eb19e56b7990662db
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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