Oxalic Acid → 3,3-Bis(4-methylphenyl)-2-propenal

HRID 1110550ノート

反応式

HRID 1110550 の反応式
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.C(NC(C)C)(C)C.C([Li])CCC.[C:29](O)(=O)[C:30](O)=[O:31]>CCCCCC.C(N=CC)(C)(C)C.ClP(=O)(OCC)OCC.O1CCCC1>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:29][CH:30]=[O:31])=[CH:4][CH:3]=1

参加物

9

反応物 4

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 691484,4'-DimethylbenzophenoneHCID 178418339Butyllithium

生成物 1

HCID 127223653,3-Bis(4-methylphenyl)-2-propenal

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 30 hours. The following reagents were used: 4,4'-dimethylbenzophenone (21 g), diisopropylamine (32.2 mL), 1.55M n-butyl lithium in hexane (143 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (17.6 mL) and tetrahydrofuran (200 ml). The work up, varied only in that the oxalic acid catalyzed hydrolysis was done overnight at room temperature, furnished 23 g of crude product which was crystallized from hexane to give 18.1 g of 3,3-bis(4-methylphenyl)-2-propenal, mp 92°-93.5° C. Anal Calcd for C17H16O: C, 86.40; H, 6.82 Found: C, 86.48; H, 6.75.

後処理

  1. customThe compound was prepared
  2. customhydrolysis
  3. waitwas done overnight at room temperature
  4. customfurnished 23 g of crude product which
  5. customwas crystallized from hexane

出典と根拠

ORDレコード
ord-3eb9491807aa442d9e330733809847bd
出典データセット
uspto-grants-1990_12
特許番号
US04975438

反応ノート

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