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Water → 4-Benzyloxy-3-cyclopentyloxybenzaldehyde

HRID 1489716
ノート
印刷プレビュー

反応式

HRID 1489716 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:24]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]1.O>CN(C)C=O.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

生成物 1

HCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehyde

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

A stirred solution of 4-benzyloxy-3-hydroxybenzaldehyde (60.9 g; that is prepared as described in Reference Example 36) in dry dimethylformamide (270 mL) under nitrogen is treated portionwise with potassium carbonate (79.5 g). After stirring at room temperature for 45 minutes, it is treated with cyclopentyl bromide (34.3 mL), and the resulting suspension is heated at 60° C. for 8 hours. After cooling, the solution is evaporated to low bulk under reduced pressure, to give an oil. This oil is treated with water (250 mL) and diethyl ether (300 mL), and the aqueous layer is washed with further quantities of diethyl ether (2×50 mL). The combined ethereal extracts are washed with brine (1×50 mL) and with water (3×50 mL), dried over magnesium sulfate and evaporated. The resulting residue is crystallized from methanol, to give 4-benzyloxy-3-cyclopentyloxybenzaldehyde (79 g), m.p. 55°-56° C. [Elemental analysis: C,77.1; H,6.9%; calculated: C,77.0; H,6.8%].

後処理

  1. customthat is prepared
  2. temperaturethe resulting suspension is heated at 60° C. for 8 hours
  3. temperatureAfter cooling
  4. customthe solution is evaporated to low bulk under reduced pressure
  5. customto give an oil
  6. washthe aqueous layer is washed with further quantities of diethyl ether (2×50 mL)
  7. washThe combined ethereal extracts are washed with brine (1×50 mL) and with water (3×50 mL)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe resulting residue is crystallized from methanol

出典と根拠

ORDレコード
ord-51c0c0481bc5468291ecbb4180212a49
出典データセット
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05679696

反応ノート

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