Formaldehyde → Methyl tropate

HRID 2255276Notes

Reaction equation

HRID 2255276 reaction equation
[C:1](=O)(O)[O-:2].[Na+].C=O.[C:8]1([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)(=O)C(O)=O>CS(C)=O>[C:15]([O:17][CH3:18])(=[O:16])[CH:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:1][OH:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 971Oxalic AcidHCID 7559Methyl phenylacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 239086Methyl tropate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A nitrogen purged 500 mL three-neck flask was charged with sodium bicarbonate (1.05 g; 0.013 mole), paraformaldehyde (17.37 g; 0.55 mole) and dimethyl sulfoxide (100 mL). Methyl phenylacetate (75.09 g; 0.5 mole) was added and rinsed in with dimethylsulfoxide (50 mL). The slurry was stirred magnetically and the temperature rose from 22° C. to 34° C. over 40 minutes. The temperature remained at 33°-34° C. for about one hour, after which the temperature was raised to 45°-46° C. and held for 12 hours. The reaction mixture was allowed to cool with stirring for about seven hours. A solution of anhydrous oxalic acid (1.13 g; 0.013 mole) in dimethylsulfoxide (6 mL) was added, and the solvent was distilled at pot temperature 45° C. to 100° C. at 0.05 mm Hg. The distillate (153.6 g) was retained. The pale yellow oily residue of crude methyl tropate (112.82 g) contained a small amount of white solid (sodium hydrogen oxalate).

Workup

  1. customA nitrogen purged 500 mL three-neck flask
  2. washrinsed in with dimethylsulfoxide (50 mL)
  3. waitThe temperature remained at 33°-34° C. for about one hour
  4. temperatureafter which the temperature was raised to 45°-46° C.
  5. waitheld for 12 hours
  6. temperatureto cool
  7. stirringwith stirring for about seven hours
  8. distillationthe solvent was distilled at pot temperature 45° C. to 100° C. at 0.05 mm Hg

Sources & evidence

ORD record
ord-07e804c3712a4e18b201b7ea4b3ddd63
Source dataset
uspto-grants-1993_08
Patent number
US05239121

Reaction notes

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