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Sodium Hydroxide → HCID 54294841、化合物

HRID 2165181
ノート
印刷プレビュー

反応式

HRID 2165181 の反応式
COCCO[AlH2-]OCCOC.[Na+].[H-].[H-].COCCO[Al+]OCCOC.[Na+].C[O:28][C:29](=O)[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]=[C:39]([CH2:41][CH2:42][CH:43]=[C:44]([CH2:46][CH2:47][CH:48]=[C:49]([CH3:51])[CH3:50])[CH3:45])[CH3:40])=[CH:32][CH:31]=1.[OH-].[Na+].[H][H]>C1(C)C=CC=CC=1.CC(O)C.O>[CH2:37]([O:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][OH:28])=[CH:35][CH:34]=1)[CH:38]=[C:39]([CH2:41][CH2:42][CH:43]=[C:44]([CH2:46][CH2:47][CH:48]=[C:49]([CH3:51])[CH3:50])[CH3:45])[CH3:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 53799950HCID 53799950、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 54294841HCID 54294841、化合物

試薬・触媒・溶媒 3

HCID 3776
Isopropanol
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

実験手順

4 g (14 mmol) Vitride®, which is 70% sodium bis-(2-methoxy-ethoxy)-aluminum dihydride, were added dropwise with stirring and cooling with ice at 5° to 15° C. to a solution of 5 g (14 mmol) 4-farnesyloxybenzoic acid methyl ester in 30 ml toluene. The mixture was then heated for 2 hours to the boiling temperature, cooled and 10% sodium hydroxide solution added dropwise while cooling with ice (until the evolution of hydrogen stopped). After approx. 10 ml water and a few drops 2-propanol had been added, the toluene phase was separated off, the aqueous phase was washed twice with toluene and, after drying with sodium sulfate, was concentrated by evaporation. The residue was chromatographed on silica gel (Merck) (eluent: methylene chloride/methanol 99:1). 4-farnesyloxybenzyl alcohol having a refractive index n20 of 1.5305 was obtained in a yield of 3.6 g (78% of the theoretical).

後処理

  1. additionwere added dropwise
  2. temperatureThe mixture was then heated for 2 hours to the boiling temperature
  3. temperaturecooled
  4. customthe toluene phase was separated off
  5. washthe aqueous phase was washed twice with toluene
  6. dry with materialafter drying with sodium sulfate
  7. concentrationwas concentrated by evaporation
  8. customThe residue was chromatographed on silica gel (Merck) (eluent: methylene chloride/methanol 99:1)

出典と根拠

ORDレコード
ord-0aedd5f44bfa4495ab3d3d07612547fb
出典データセット
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04939171

反応ノート

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