Perchloric Acid → Methyl 4-acetyl-4-methoxycarbonyl-3-formyl-6-nonynoate

HRID 972100Notes

Reaction equation

HRID 972100 reaction equation
[C:1]([C:4]([C:21]([O:23][CH3:24])=[O:22])([CH2:16][C:17]#[C:18][CH2:19][CH3:20])[CH:5]([CH:11](OC)[O:12]C)[CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:1]([C:4]([C:21]([O:23][CH3:24])=[O:22])([CH2:16][C:17]#[C:18][CH2:19][CH3:20])[CH:5]([CH:11]=[O:12])[CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 20387581Methyl 4-acetyl-4-methoxycarbonyl-3-dimethoxymethyl-6-nonynoate

Product 1

HCID 20387588Methyl 4-acetyl-4-methoxycarbonyl-3-formyl-6-nonynoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-acetyl-4-methoxycarbonyl-3-dimethoxymethyl-6-nonynoate (530 mg) is dissolved in 20 ml of tetrahydrofuran, and 25 ml of 1% aqueous solution of perchloric acid is added to the solution. The mixture is stirred at 26° to 28° C. for 12 hours. Subsequently the reaction mixture is neutralized with sodium bicarbonate and concentrated in a vacuum. The residue is extracted with ethyl acetate. The extract is dried and then concentrated to give methyl 4-acetyl-4-methoxycarbonyl-3-formyl-6-nonynoate (compound (3), R1 =R2 =CH3) in a yield of 98.3%.

Workup

  1. concentrationconcentrated in a vacuum
  2. extractionThe residue is extracted with ethyl acetate
  3. customThe extract is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-974062da86f14e378f717d85ec0ce327
Source dataset
uspto-grants-1979_07
Patent number
US04163111

Reaction notes

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