Oxalic Acid → p-METHOXYCINNAMALDEHYDE

HRID 2232797노트

반응식

HRID 2232797 반응식
[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

참가 물질

9

반응물 4

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 312444-MethoxybenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 641294p-METHOXYCINNAMALDEHYDE

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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-e38de0b036fd4f89825b5d8a85a8341e
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04788206

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