Methanol → Methyl phenylacetate

HRID 1439800Notes

Reaction equation

HRID 1439800 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O-:10].[Na+].[CH3:12][OH:13]>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[CH3:9][O:10][C:12](=[O:13])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7503Benzyl ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 7559Methyl phenylacetateYield 95.4%

Reagents, catalysts & solvents 1

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)Catalyst

Conditions

Temperature
35 °C

Procedure

6 g of cobalt octacarbonyl was added to 100 ml of methanol. Then CO was passed through with stirring (500 rpm) at 35° C for 30 minutes with an excess pressure of 600 mm Hg. Then the mixture was heated to 55° C and, with a steady feed-through of CO, 190 g (1.5 mole) of benzyl chloride and 329 g of 25.8 wt-% sodium methylate were fed in over a period of 3 hours at a stirring speed of 500 to 750 rpm. Carbon monoxide delivery continued for about 21/2 more hours until no further absorption took place. Then water was mixed with the reaction mixture and it was extracted with ether. After distilling the ether a reaction mixture was obtained from which 215 g of phenylacetic acid methyl ester in a purity of 97.03% was obtained by distillation (yield 95.4%).

Workup

  1. customwere fed in over a period of 3 hours at a stirring speed of 500 to 750 rpm
  2. customCarbon monoxide delivery continued for about 21/2 more hours until no further absorption
  3. additionThen water was mixed with the reaction mixture and it
  4. extractionwas extracted with ether
  5. distillationAfter distilling the ether a reaction mixture

Sources & evidence

ORD record
ord-6cb61b2b3502452aa355260ef99b7596
Source dataset
uspto-grants-1977_11
Patent number
US04060690

Reaction notes

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