Arotinoic methanol → p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzaldehyde

HRID 2286099Notes

Reaction equation

HRID 2286099 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:24])=[CH:15]/[C:16]3[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2>CCOCC.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:24])=[CH:15]/[C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 1

HCID 6438709Arotinoic methanol

Product 1

HCID 86738348p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

6.7 g of p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzyl alcohol (prepared as described in Example 12) dissolved in 100 ml of absolute ether are added dropwise within 10 minutes to a stirred suspension, cooled to 0°-5° C., of manganese dioxide in 100 ml of absolute ether. The mixture is stirred at room temperature overnight and then filtered through Celite. The filtrate is concentrated to dryness on a rotary evaporator. The yellowish oil crystallizes. Recrystallisation from ether yields p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]-benzaldehyde in the form of colourless crystals of melting point 140°-141° C.

Workup

  1. additionare added dropwise within 10 minutes to a stirred suspension
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate is concentrated to dryness on a rotary evaporator
  4. customThe yellowish oil crystallizes
  5. customRecrystallisation from ether

Sources & evidence

ORD record
ord-9eea998401704ec6bc07c157a2ae795e
Source dataset
uspto-grants-1982_04
Patent number
US04326055

Reaction notes

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