Sulfuric Acid → 3,3-Dimethylhex-5-enal

HRID 1361909Notes

Reaction equation

HRID 1361909 reaction equation
S(=O)(=O)(O)O.C[O:7][CH:8]=[CH:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH:12]=[CH2:13].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:14][C:10]([CH3:15])([CH2:11][CH:12]=[CH2:13])[CH2:9][CH:8]=[O:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 855664661-Methoxy-3,3-dimethylhexa-1,5-diene

Product 1

HCID 110623943,3-Dimethylhex-5-enal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 500-mL round-bottom flask, sulfuric acid (48 mL; 30%) was added to a stirred tetrahydrofuran (150 mL) solution of 1-methoxy-3,3-dimethylhexa-1,5-diene (15.89 g, 0.113 mol). After the mixture had been stirred for 1 hour, it was gradually poured into saturated sodium bicarbonate (ca. 500 mL), and then extracted with diethyl ether (4×200 mL). The combined extracts were washed with brine, dried over sodium sulfate, and filtered. Evaporation of the solvent gave the title compound as a pale yellow liquid.

Workup

  1. extractionextracted with diethyl ether (4×200 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bda55076e78c4968abca1e6f4ba79903
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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