Potassium Carbonate → 2-Methyl-1,6-dioxaspiro[4.4]nonane-2-carbaldehyde

HRID 647753Notes

Reaction equation

HRID 647753 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][CH2:17]2)[O:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:12][C:13]1([CH:14]=[O:9])[CH2:22][CH2:21][C:16]2([CH2:17][CH2:18][CH2:19][O:20]2)[O:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 132371808-Methyl-1,6-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 132371812-Methyl-1,6-dioxaspiro[4.4]nonane-2-carbaldehydeYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled and stirred solution of 8.80 g of 85% m-chloroperbenzoic acid in 120 ml of methylene chloride was added 6.16 g of 8-methyl-1,6-dioxaspiro[4.5]dec-7-ene in 20 ml of methylene chloride. The exothermic reaction was kept below 15° C. After 15 minutes, the mixture was poured into 600 ml of saturated potassium carbonate. The resulting organic layer was then washed with aqueous base, dried and distilled to yield 4.37 g of the desired product as a colorless liquid, b.p. 65°-70° C. (1 torr.).

Workup

  1. temperatureTo a cooled
  2. customThe exothermic reaction
  3. customwas kept below 15° C
  4. washThe resulting organic layer was then washed with aqueous base
  5. customdried
  6. distillationdistilled

Sources & evidence

ORD record
ord-725b9442162c4025a7776122a87bc63e
Source dataset
uspto-grants-1983_10
Patent number
US04410354

Reaction notes

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