Oxalic Acid → 3,3-Bis(2-fluorophenyl)-2-propenal

HRID 1110487Notes

Reaction equation

HRID 1110487 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=O.ClP(=O)(OCC)[O:19][CH2:20][CH3:21].O1CCCC1.C(O)(=O)C(O)=O>CCCCCC.C(N=CC)(C)(C)C>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[CH:21][CH:20]=[O:19]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 8028TetrahydrofuranHCID 13139Diethyl chlorophosphateHCID 676492,2'-Difluorobenzophenone

Product 1

HCID 143472273,3-Bis(2-fluorophenyl)-2-propenal

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 138901N-Ethylidene-2-methylpropan-2-amineSolvent

Conditions

Temperature
85 °C

Procedure

The compound was prepared according to the procedure described in Example 84. The following reagents were used: 2,2'-difluorobenzophenone (6.0 g) diisopropylamine (28.8 mL) 1.6M n-butyl lithium in hexane (129 mL), acetaldehyde N-tert-butylimine (13.2 mL). diethyl chlorophosphonate (14.85 mL) and tetrahydrofurane (100 mL). The reaction was worked up in the usual manner, with the exception that the oxalic acid catalyzed hydrolysis was slow and it was necessary to heat the mixture to 85° C. for one hour to complete the conversion. The crude product (5.8 g), obtained as an orange oil, was crystallized from hexane to give 4.6 g of 3,3-bis(2-fluorophenyl)-2-propenal mp 75°-77.° C. Anal. Calculated for : C15H10F2O: C. 73.76; H, 4.13; F, 15.56 Found: C, 73.32; H, 4.27; F, 15.74.

Workup

  1. customThe compound was prepared
  2. customhydrolysis
  3. customThe crude product (5.8 g), obtained as an orange oil
  4. customwas crystallized from hexane

Sources & evidence

ORD record
ord-f5dda7a4e63d498db09664db37894cbc
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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