4-Hydroxybenzaldehyde → p-Octyloxycarbonyloxybenzaldehyde

HRID 845707ノート

反応式

HRID 845707 の反応式
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:3].[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH2:5]([O:4][C:2]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)=[O:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

参加物

4

反応物 2

HCID 1264-HydroxybenzaldehydeHCID 81956Carbonochloridic acid, octyl ester

生成物 1

HCID 13828007p-Octyloxycarbonyloxybenzaldehyde収率 99.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Octyl chloroformate (23.1 g, 0.12 mol) was added to and reacted with a solution of p-hydroxybenzaldehyde (III) (16 g, 0.18 mol) dissolved in dry pyridine (100 ml), followed by allowing the reaction mixture to stand overnight, thereafter extracting it with toluene, washing the organic layer with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution and further with water until the washing water became neutral, and distilling off toluene to obtain p-octyloxycarbonyloxybenzaldehyde (IV) (33.2 g), dissolving this compound (20.5 g, 0.07 mol) in acetic acid (60 ml), dropwise adding a solution of anhydrous chromic acid (14 g, 0.14 mol) dissolved in water (11 ml) and acetic (17 ml) to the above solution being agitated, keeping the inner temperature at 40° C. on a water bath for 4 hours after completion of the dropwise addition, thereafter cooling the reaction mixture, adding water (300 ml), filtering the deposited crystals, recrystallizing from ethanol to obtain p-hexyloxycarbonyloxybenzoic acid (V) (7 g), adding thereto thionyl chloride (10 ml), heating the mxiture under reflux for one hour, and distilling off excess thionyl chloride to obtain the objective p-hexyloxycarbonyloxybenzoic acid chloride (VI) (7.5 g).

後処理

  1. extractionextracting it with toluene
  2. washwashing the organic layer with 6N-hydrochloric acid
  3. distillationdistilling off toluene

出典と根拠

ORDレコード
ord-e36a5b41098541d3a1f9617c56a320ec
出典データセット
uspto-grants-1988_07
特許番号
US04759869

反応ノート

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