Hydrochloric Acid → HCID 15479425, compound

HRID 1954073Notes

Reaction equation

HRID 1954073 reaction equation
C(O[C:4](OCC)([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=1)[C:5](=[O:7])[CH3:6])C.Cl.C1C[O:30]CC1>>[CH3:18][O:17][C:15]1[CH:16]=[C:11]([CH2:10][CH2:9][CH2:8][CH2:4][C:5](=[O:7])[CH:6]=[O:30])[CH:12]=[C:13]([O:21][CH3:22])[C:14]=1[O:19][CH3:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 131722004HCID 131722004, compound

Product 1

HCID 15479425HCID 15479425, compound

Procedure

To a solution 1.8 g of 6-(3,4,5-trimethoxyphenyl)-2-keto-3-hexanal-diethylacetal in 15 ml of THF was added sufficient 6N HCl so that the pH<1. this mixture was refluxed for 18 hours. the mixture was cooled to room temperature and the solvent evaporated. the residue was triturated with 50 ml of ethyl acetate, the ethyl acetate solution dried with sodium sulfate (Na2SO4) and evaporated. the residue was chromatographed on 30 g of silica using CHCl3 as the elutant. Appropriate fractions were combined and evaporated to yield 0.8 g of 6-(3,4,5-trimethoxyphenyl)-2-keto-hexanal as an oil. 1H NMR: (CDCl3) δ 9.15 (s, 1 H), 6.40 (s, 2 H), 3.80 (s, 6 H), 3.76 (s, 3 H), 2.50 (m, 4 H), 1.60 (m, 4 H).

Workup

  1. temperaturethis mixture was refluxed for 18 hours
  2. customthe solvent evaporated
  3. customthe residue was triturated with 50 ml of ethyl acetate
  4. dry with materialthe ethyl acetate solution dried with sodium sulfate (Na2SO4)
  5. customevaporated
  6. customthe residue was chromatographed on 30 g of silica
  7. customevaporated

Sources & evidence

ORD record
ord-3b8434ae17d0454f808e1e5f3c3d736a
Source dataset
uspto-grants-2000_09
Patent number
US06121280

Reaction notes

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