Red-Al → HCID 69324125, compound

HRID 1926569Notes

Reaction equation

HRID 1926569 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH3:13][C:14]1([CH3:31])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH:29]=[O:30])[CH2:26][CH2:25][C:24]([CH3:27])=[CH:23][CH:22]1[CH3:28]>C1(C)C=CC=CC=1>[CH3:31][C:14]1([CH3:13])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH2:29][OH:30])[CH2:26][CH2:25][C:24]([CH3:27])=[CH:23][CH:22]1[CH3:28]

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 86761569HCID 86761569, compound

Product 1

HCID 69324125HCID 69324125, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
21.200000762939453 °C

Procedure

A 3-L reaction flask equipped with a stirrer, a thermometer, a reflux condenser, a heating mantle, and an addition funnel was charged with Vitride (1112 g, 3.5 mol) and toluene (1 Kg). The resulting mixture was stirred at 21.2° C. The Diels-Alder product containing 1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2,4-dimethyl-cyclohex-3-enecarbaldehyde (778.5 g, 2.59 mol, synthesized as above in EXAMPLE XI) was added over about 4 hours. The temperature was allowed to rise to 35° C. The reaction mass was aged for 1 hour. The excessive Vitride reagent was quenched with ethyl acetate (125 g), followed by sodium hydroxide (30%, 3 Kg). The temperature was allowed to rise to 40° C. and stirred for another 0.5 hours. The organic phase was washed with hot water (1 L) twice and distilled to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2,4-dimethyl-cyclohex-3-enyl]-methanol (829.5 g).

Workup

  1. customequipped with a stirrer
  2. additionwas added over about 4 hours
  3. customto rise to 35° C
  4. customThe excessive Vitride reagent was quenched with ethyl acetate (125 g)
  5. customto rise to 40° C.
  6. stirringstirred for another 0.5 hours
  7. washThe organic phase was washed with hot water (1 L) twice
  8. distillationdistilled

Sources & evidence

ORD record
ord-cf1f2f45d3d84604bb12711fd1daaf21
Source dataset
uspto-grants-2012_05
Patent number
US08183200B1

Reaction notes

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