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

HRID 1110550노트

반응식

HRID 1110550 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 13139Diethyl chlorophosphate용매HCID 138901N-Ethylidene-2-methylpropan-2-amine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3eb9491807aa442d9e330733809847bd
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975438

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