Dimethylformamide → HCID 57857231, compound

HRID 503661Notes

Reaction equation

HRID 503661 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=1.O=P(Cl)(Cl)Cl.CN([CH:32]=[O:33])C>>[CH2:17]([O:16][C:4]1[CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[C:2]([Cl:1])[C:3]=1[CH:32]=[O:33])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 14784148HCID 14784148, compound

Product 1

HCID 57857231HCID 57857231, compoundYield 63%

Procedure

12 g of chloro-3,5-dibenzyloxybenzene are dissolved in 40 ml of DMF. 12 ml of POCl3 are slowly added dropwise at 5-10°. The mixture is allowed to react further for 90 min at room temperature, then overnight at 80° C. The solution is evaporated in a Rotavapor, then added to 200 ml of icewater. The mixture is extracted 3× with EtOAc, washed with water, dried and evaporated. Silica gel chromatography gives 8.2 g (63%) of 2,4-bisbenzyloxy-6-chlorobenzaldehyde, which crystallises from (Me2C)2O, m.p. 85-86°.

Workup

  1. customto react further for 90 min at room temperature
  2. customovernight
  3. customat 80° C
  4. customThe solution is evaporated in a Rotavapor
  5. additionadded to 200 ml of icewater
  6. extractionThe mixture is extracted 3× with EtOAc
  7. washwashed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-f0e928ce074a467e82d8c3c0a6f8b88e
Source dataset
uspto-grants-2010_08
Patent number
US07776920B2

Reaction notes

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