Pentylbenzene → 6-Oxo-6-(4-pentylphenyl)hexanoic acid

HRID 1720137

反応式

HRID 1720137 の反応式
CO[C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].S(Cl)(Cl)=O.[CH2:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH2:19][CH3:20].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>C(O)C>[CH2:16]([C:21]1[CH:22]=[CH:23][C:24]([C:3]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:11])=[CH:25][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH3:20]

参加物

7

反応物 5

HCID 10864PentylbenzeneHCID 12328monoMethyl adipateHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 152955596-Oxo-6-(4-pentylphenyl)hexanoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Adipic acid monomethyl ester (35 g; 0.44 mole) is converted to the acid chloride with thionyl chloride (50 g) in a manner analogous to that described in Example 1. This product is reacted with pentylbenzene (400 ml) and aluminum chloride (80 g) and the reaction product isolated as a colorless oil (25 g; b.p. 165°-174° C. @0.15 mm) and identified as methyl 5-(4-n-pentylbenzoyl) pentanoate. This ester (5 g; 0.017 mole) is hydrolysed with sodium hydroxide in aqueous ethanol and the product isolated as in Example 1. Recrystallization from aqueous ethanol gives 5-(4-n-pentylbenzoyl)pentanoic acid (4.0 g) as colorless crystals, m.p. 84°-86° C.

後処理

  1. customthe reaction product isolated as a colorless oil (25 g; b.p. 165°-174° C. @0.15 mm)
  2. customthe product isolated as in Example 1
  3. customRecrystallization from aqueous ethanol

出典と根拠

ORDレコード
ord-51f7c4be389a45bdb198c848b9091a7e
出典データセット
uspto-grants-1996_04
特許番号
US05504244

関連ノート

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