Formaldehyde → (5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)oxirane

HRID 346286Notes

Reaction equation

HRID 346286 reaction equation
C(C1C=CC(NCC([C:16]2[CH:25]=[CH:24][C:23]3[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:29])([CH3:28])[C:18]=3[CH:17]=2)O)=CC=1)(OCC)=O.P([O-])([O-])O.[Na+].[Na+].C=O.[O:38]1[CH2:43][CH2:42]OCC1>>[CH3:27][C:22]1([CH3:26])[CH2:21][CH2:20][C:19]([CH3:28])([CH3:29])[C:18]2[CH:17]=[C:16]([CH:42]3[CH2:43][O:38]3)[CH:25]=[CH:24][C:23]1=2

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 312751,4-DioxaneHCID 14726540N-(4-carbethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-aminoethanolHCID 177427533Disodium;hydrogen phosphite

Product 1

HCID 14726539(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)oxirane

Procedure

1.58 g (4 millimoles) of N-(4-carbethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-aminoethanol were stirred with 20 ml of 1N sodium hydrogen phosphite solution and 2 ml (20 millimoles) of formalin solution in 20 ml of dioxane for 1 hour at 60° C. The mixture was then poured onto water and extracted with ether, and the organic phase was washed with 2N sodium hydroxide solution and water, dried over magnesium sulfate and evaporated down. Recrystallization from methanol gave 1.0 g of the title compound, RF =0.51 (thin layer chromatography, silica gel; 7:1 n-heptaneethyl acetate).

Workup

  1. additionThe mixture was then poured onto water
  2. extractionextracted with ether
  3. washthe organic phase was washed with 2N sodium hydroxide solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-31963568ccef4ae7a5c8167435ebb438
Source dataset
uspto-grants-1991_10
Patent number
US05061705

Reaction notes

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