Sulfuric Acid → HCID 58972226, compound

HRID 922072Notes

Reaction equation

HRID 922072 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][CH2:19][C:20]#N.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.[OH:39]S(O)(=O)=O>CC(OC)(C)C.O>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][CH2:19][CH:20]=[O:39]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 14487Diisobutylaluminum hydrideHCID 58972229HCID 58972229, compound

Product 1

HCID 58972226HCID 58972226, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

(E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-enenitrile (178 mg, 0.59 mmol) was dried azeotropically with toluene in vacuo (3×2 mL), redissolved into toluene (3 mL) and cooled to 0° C. DIBALH (1.0 M in heptane, 0.9 mmol) was added over 3 minutes dropwise. After 1 h, H2O (2 ml) and aqueous H2SO4 (6 mL 2.5 M) were added and the mixture let warm to room temperature for 2.5 h. MTBE (5 mL) was added, the layers separated and the aqueous phase extracted 3×5 mL MTBE. The combined organics were washed with brine (10 mL), dried over anhydrous Na2SO4 and concentrated to give (E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-enal as a colorless oil.

Workup

  1. temperaturethe mixture let warm to room temperature for 2.5 h
  2. customthe layers separated
  3. extractionthe aqueous phase extracted 3×5 mL MTBE
  4. washThe combined organics were washed with brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a4bfb667326b40af851e3b38837e1627
Source dataset
uspto-grants-2016_03
Patent number
US09278085B2

Reaction notes

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