Formaldehyde → 2,2,3-Trimethyl-alpha-methylene-3-cyclopentene-1-acetaldehyde

HRID 1377434ノート

反応式

HRID 1377434 の反応式
[OH-].[Na+].C=O.[CH3:5]CCCCC.[CH3:11][C:12]1[C:16]([CH3:18])([CH3:17])[CH:15]([CH2:19][CH:20]=[O:21])[CH2:14][CH:13]=1>CO.O>[CH3:18][C:16]1([CH3:17])[C:12]([CH3:11])=[CH:13][CH2:14][CH:15]1[C:19](=[CH2:5])[CH:20]=[O:21]

参加物

7

反応物 4

HCID 712FormaldehydeHCID 8058HexaneHCID 14798Sodium HydroxideHCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

生成物 1

HCID 202354022,2,3-Trimethyl-alpha-methylene-3-cyclopentene-1-acetaldehyde収率 215.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A 3 liter 3 neck round bottomed flask was charged with 50 g of sodium hydroxide (1.25 moles) in 250 g of methanol. 200 g of paraformaldehyde, 500 g of hexane and 2.5 g of BHA were added and the flask was cooled to 0° C. With fast agitation 500 g of campholenic aldehyde at a purity of 88.9% (2.92 moles) were added dropwise over 70 minutes keeping the temperature at 0°-5° C. The batch was stirred for 3 hours at 0° C. Then 50 ml of water was added and the layers are separated. The water layer was back extracted with 250 ml of hexane. The hexane extracts were combined and washed with 2×500 ml of 10% sodium hydroxide and 3×500 ml of water. The batch was dried and afforded 1163 g of crude 2-(2,2,3-trimethylcyclopent-3-en-1-yl)propenal in hexane. A second batch was prepared analogously affording 1169 g of crude product.

後処理

  1. customat 0°-5° C
  2. customthe layers are separated
  3. extractionThe water layer was back extracted with 250 ml of hexane
  4. washwashed with 2×500 ml of 10% sodium hydroxide and 3×500 ml of water
  5. customThe batch was dried

出典と根拠

ORDレコード
ord-ff6e6567146a41b18082fdf0e2afd122
出典データセット
uspto-grants-1997_09
特許番号
US05665696

反応ノート

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