Formic Acid → Formate

HRID 1763407Notes

Reaction equation

HRID 1763407 reaction equation
[CH3:1][C:2]1[CH:7]([OH:8])[CH2:6][C:4](=[O:5])[C:3]=1[CH2:9][CH:10]=[CH2:11].[CH:12]([OH:14])=[O:13]>C(Cl)(Cl)Cl>[CH:12]([O-:14])=[O:13].[CH3:1][C:2]1[CH:7]([OH:8])[CH2:6][C:4](=[O:5])[C:3]=1[CH2:9][CH:10]=[CH2:11]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-3×

Product 2

HCID 283FormateHCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
102 °C

Procedure

38 kg of a mixture of 60% (R) allethrolone and 40% of (S) allethrolone resulting from the industrial resolution of racemic allethrolone and having a specific rotation [α]D20 = -7.5° C (c = 10% in chloroform) and the proportion of which is shown by its circular dichroism, were added to 190 liters of formic acid and the mixture refluxed with stirring under nitrogen at a temperature of about 102° C for 26 hours. The mixture was cooled and residual formic acid was distilled under reduced pressure to obtain raw formate of racemic (R,S) allethrolone which was used as is for the next step.

Workup

  1. temperaturethe mixture refluxed
  2. temperatureThe mixture was cooled
  3. distillationresidual formic acid was distilled under reduced pressure

Sources & evidence

ORD record
ord-a13cbc6f162649cd8c910b2a96c86566
Source dataset
uspto-grants-1978_09
Patent number
US04111993

Reaction notes

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