Dimethyl Sulfate → 2-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-1-methoxy-3,5,5,8,8-pentamethyl-

HRID 364763

反応式

HRID 364763 の反応式
[OH-].[Na+].[CH:3]([C:5]1[C:14]([CH3:15])=[CH:13][C:12]2[C:11]([CH3:17])([CH3:16])[CH2:10][CH2:9][C:8]([CH3:19])([CH3:18])[C:7]=2[C:6]=1[OH:20])=[O:4].S(OC)(O[CH3:25])(=O)=O>O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[CH:3]([C:5]1[C:14]([CH3:15])=[CH:13][C:12]2[C:11]([CH3:16])([CH3:17])[CH2:10][CH2:9][C:8]([CH3:19])([CH3:18])[C:7]=2[C:6]=1[O:20][CH3:25])=[O:4]

参加物

7

反応物 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 190951662-Formyl-1-hydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene

生成物 1

HCID 1747662-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-1-methoxy-3,5,5,8,8-pentamethyl-収率 78.7%

試薬・触媒・溶媒 3

HCID 21218Trioctylmethylammonium chloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Methylation. A solution of sodium hydroxide (0.98 g, 0.0244 mol) in water (24 mL) was added in one portion to a solution of 2-formyl-1-hydroxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene (3 g, 0.0122 mol), dimethyl sulfate (3.07 g, 0.0244 mol) and Adogen 464* (0.56 g) in methylene dichloride (48 mL). The mixture was stirred vigorously at 38°-40° C. for 4 h. After cooling, the organic layer was separated, washed with brine (3×20 mL) and dried (Na2SO4). The solvent was removed by distillation and the residue was distilled to yield 2-formyl-1-methoxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene (3a), (2.5 g), mp 78° C. (from hexane), GLC purity 99.7%, exhibiting the expected spectral data.

後処理

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. washwashed with brine (3×20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed by distillation
  6. distillationthe residue was distilled

出典と根拠

ORDレコード
ord-67296d13849c4d219f68661693c23ecc
出典データセット
uspto-grants-1986_08
特許番号
US04605778

関連ノート

読み込み中…