Methanol → HCID 14446273, compound

HRID 486417Notes

Reaction equation

HRID 486417 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[C:9]([CH3:12])[CH:10]=2)[C:5]([CH3:15])([CH3:14])[CH:4]([CH3:16])[CH:3]1[CH3:17].C[OH:20]>>[CH:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[CH3:13])[C:5]([CH3:15])([CH3:14])[CH:4]([CH3:16])[CH:3]([CH3:17])[C:2]2([CH3:18])[CH3:1])=[O:20]

Participants

3

Reactant 2

HCID 887Methanol2×HCID 144462711,2,3,4-Tetrahydro-1,1,2,3,4,4,6,7-octamethylnaphthalene

Product 1

HCID 14446273HCID 14446273, compound

Conditions

Temperature
50 °C

Procedure

To prepare the corresponding 6-carboxaldehyde, 16 portions of Ce(NH4)2 (NO3)6 (16×16.0 g=256.0 g) in methanol (16×100 ml) is added to a solution of 1,1,2,3,4,4,6,7-octamethyl-1,2,3,4-tetrahydronaphthalene (16.0 g) in methanol (700 ml), over 8 hrs, while maintaining the temperature at 50° C. After about 1/2 of the methanol is evaporated, the resulting product is extracted with petroleum ether 30° C.-50° C./saturated NaCl. After crystallizing in ethanol, treating the mother liquors and recrystallizing, the desired 6-carboxaldehyde, 6-formyl-1,1,2,3,4,4,7-heptamethyl-1,2,3,4-tetrahydronaphthalene is obtained.

Workup

  1. customAfter about 1/2 of the methanol is evaporated
  2. extractionthe resulting product is extracted with petroleum ether 30° C.-50° C./saturated NaCl
  3. customAfter crystallizing in ethanol
  4. additiontreating the mother liquors
  5. customrecrystallizing

Sources & evidence

ORD record
ord-a6b569ce02c7481fb2fcace0be910378
Source dataset
uspto-grants-1994_03
Patent number
US05292719

Reaction notes

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