Methyl Acrylate → Methyl 5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-carboxylate

HRID 364985Notes

Reaction equation

HRID 364985 reaction equation
[C:1](OC)(=O)[CH:2]=[CH2:3].[CH3:7][CH2:8][C@@H:9]1[C@@H:14]2[CH2:15][C@@H:16]([C@H:17](O)[C:18]3C=CN=C4C=3C=C(OC)C=C4)N(C[CH2:13]2)C1.[C:31]([O:34][C:35](=[O:37])[CH3:36])(=O)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:3])[CH2:7][CH2:8][CH2:9][C:14]2([CH3:13])[C:15]1=[CH:16][CH:17]=[CH:18][CH:36]2[C:35]([O:34][CH3:31])=[O:37]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 7918Acetic AnhydrideHCID 121515(-)-Dihydroquinine

Product 1

HCID 20239095Methyl 5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.86 g (20 mM) of the amine obtained according to letter b above, 3.44 g (40 mM) of methyl acrylate in 20 ml of toluene containing 20 mg of hydroquinine was heated in an autoclave of stainless steel under nitrogen at 150° during 3 h. Then, 4.1 g (40 mM) of acetic anhydride were added and the mixture was heated at 150° during 1 h. The evaporation of the solvent and distillation of the residue gave 3.95 g (yield: 84%) of the desired ester; bp 160°-180°/2.66 Pa.

Workup

  1. temperaturethe mixture was heated at 150° during 1 h
  2. customThe evaporation of the solvent and distillation of the residue

Sources & evidence

ORD record
ord-a75111911ff94181bc90842bbf5fcd39
Source dataset
uspto-grants-1986_08
Patent number
US04607109

Reaction notes

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