Methanol → Methyl phenylacetate

HRID 1439795Notes

Reaction equation

HRID 1439795 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:17][O-:18].[Na+].[C]=O.[CH3:22][OH:23]>[Mn].O>[CH3:17][O:18][C:22](=[O:23])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 7503Benzyl ChlorideHCID 24489Sodium DithioniteHCID 10942334Sodium MethoxideHCID 178418416HCID 178418416, compound

Product 1

HCID 7559Methyl phenylacetateYield 85.4%

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

6 H2O, 2 g manganese powder (150 μ) and 1 g Na2S2O4 were added to 100 ml of methanol in a CO atmosphere. Then CO was passed through the mixture with stirring (500 rpm) at 35° C for 30 minutes with an overpressure of 600 mm Hg. At 55° C, 190 g of benzyl chloride was added to the reaction mixture. Then, over a period of 3 hours with the steady passage of CO, 355 g of 24 wt-% sodium methylate solution was fed in with a stirring speed of 500 to 750 rpm. Carbon monoxide was introduced for another 21/2 hours, approximately, until no more absorption took place. Then water was added to the mixture and the latter was separated from the manganese. The mixture was extracted with ether. After the ether was removed by distillation there remained a reaction mixture from which 3.5 g of benzyl chloride and 189 g of phenylacetic acid methyl ester (yield 85.4%) were isolated by distillation.

Workup

  1. customapproximately, until no more absorption
  2. additionThen water was added to the mixture
  3. customthe latter was separated from the manganese
  4. extractionThe mixture was extracted with ether
  5. customAfter the ether was removed by distillation

Sources & evidence

ORD record
ord-8daf4f3b857a4a488987a6c97b752d71
Source dataset
uspto-grants-1977_11
Patent number
US04060690

Reaction notes

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