Hydrochloric Acid → HCID 76842371, compound

HRID 2115631Notes

Reaction equation

HRID 2115631 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:15])[CH:13]=[O:14])=[CH:3][CH2:4][O:5][C:6](=[O:8])[CH3:7].CC(=CC)C.P([O-])(O)(O)=[O:22].[Na+].Cl([O-])=O.[Na+].Cl>C(O)(C)(C)C.O.C(OCC)(=O)C>[C:6]([O:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:15])[C:13]([OH:22])=[O:14])(=[O:8])[CH3:7]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 566095533,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate

Product 1

HCID 76842371HCID 76842371, compoundYield 130.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of aldehyde 230a (19.5 g, 92.7 mmol) in 300 mL of tert-butyl alcohol was added 2-methyl-2-butene (98.0 mL, 925 mmol). To this was added a solution of sodium dihydrogen phosphate (44.5 g, 371 mmol) in 300 mL of water. Sodium chlorite (33.6 g, 371 mmol) was added in several portions. The resulting mixture was rapidly stirred overnight at room temperature. Ethyl acetate was added and the aqueous layer was acidified to pH 3 by addition of 1 M HCl. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine, dried over MgSO4, and reduced to dryness in vacuo. The crude product (27.4 g, 121 mmol, >100% yield) was used in the next step without further purification:

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-6142d84143944cc7980a8b7a974a360a
Source dataset
uspto-grants-2008_10
Patent number
US07435861B2

Reaction notes

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