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

HRID 2232732Notes

Reaction equation

HRID 2232732 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.C(N=CC)(C)(C)C.ClP(=O)(OCC)[O:26][CH2:27][CH3:28].C(O)(=O)C(O)=O>CCCCCC.O1CCCC1>[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:28][CH:27]=[O:26]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 13139Diethyl chlorophosphateHCID 676492,2'-DifluorobenzophenoneHCID 138901N-Ethylidene-2-methylpropan-2-amine

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

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.

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-3ae034e6826a4265af0cf817f1269843
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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