Oxalic Acid → p-METHOXYCINNAMALDEHYDE

HRID 2232797ノート

反応式

HRID 2232797 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C(NC(C)C)(C)C.C([Li])CCC.[C:23](O)(=O)[C:24](O)=[O:25]>CCCCCC.C(N=CC)(C)(C)C.ClP(=O)(OCC)OCC.O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:23]/[CH:24]=[O:25])=[CH:5][CH:4]=1

参加物

9

反応物 4

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 312444-MethoxybenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 641294p-METHOXYCINNAMALDEHYDE

試薬・触媒・溶媒 4

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 13139Diethyl chlorophosphate溶媒HCID 138901N-Ethylidene-2-methylpropan-2-amine溶媒

実験手順

The compound was prepared according to the procedure described in Example 84 except that the reaction was worked up after 3 days. The following reagents were used: 4-methoxybenzaldehyde (13.5 g), diisopropylamine (32.2 mL). 1.6M n-butyl lithium in hexane (143 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofuran (200 mL). The work up, varied only in that the oxalic acid catalyzed hydrolysis was done overnight at room temperature and then at 85° C. for 2 hours, furnished 12.5 g of crude product which was crystallized from ether-hexane to yield 10 g of (E)-3-(4-methoxyphenyl)-2-propenal, mp 58.5°-60° C.

後処理

  1. customThe compound was prepared
  2. customhydrolysis
  3. waitwas done overnight at room temperature
  4. waitat 85° C. for 2 hours
  5. customfurnished 12.5 g of crude product which
  6. customwas crystallized from ether-hexane

出典と根拠

ORDレコード
ord-e38de0b036fd4f89825b5d8a85a8341e
出典データセット
uspto-grants-1988_11
特許番号
US04788206

反応ノート

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