1-Propanol → HCID 22475218, compound

HRID 2103121Notes

Reaction equation

HRID 2103121 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([F:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)CC>CC(C)=O>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:12]([C:13]([OH:28])=[O:14])=[C:11]([F:25])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 563591HCID 563591, compoundHCID 131709961Jones' reagent

Product 1

HCID 22475218HCID 22475218, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 4,5-bis-benzyloxy-2-fluoro-benzaldehyde (2.15 g, 6.39 mmol) in acetone (86.0 mL) was slowly added Jones reagent (4.3 mL). The reaction mixture was stirred 19 h at 0° C. Propanol (0.43 mL) was added and the reaction mixture was stirred 40 min at 20° C. The crude mixture was filtered, washed with acetone and poured into water (50 mL). The solid was filtered, washed with water and dried in vacuo, yielding the title compound (1.82 g, 81%) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred 40 min at 20° C
  2. filtrationThe crude mixture was filtered
  3. washwashed with acetone
  4. additionpoured into water (50 mL)
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6280dc4e444f46e6994aacd455071ae1
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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