Water → HCID 54302645, compound

HRID 1177847Notes

Reaction equation

HRID 1177847 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].F[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.O>CN(C=O)C.CCCCCC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 54302645HCID 54302645, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

4-Benzyloxy-phenol (500 mg, 2.50 mmol) was dissolved in 7 mL of DMF. K2CO3 (414 mg 3.00 mmol) was added and the resulting mixture was stirred at room temperature for 10 mins. 4-Fluorobenzaldehyde (371 mg, 3.00 mmol) was added and the resulting mixture was stirred at 50° C. for 2 hours. The reaction mixture was then heated to 80° C. for 3 hours. Water was then added and the product was extracted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 710 mg of crude product. Purification by column chromatography (using silica gel of mesh size of 60-120 and 3/97 EtOAc:Hexane as the eluent) afforded 550 mg (72% yield) of 4-(4-Benzyloxy-phenoxy)-benzaldehyde. LC-MS purity: 99.5%

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 2 hours
  2. temperatureThe reaction mixture was then heated to 80° C. for 3 hours
  3. extractionthe product was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford 710 mg of crude product
  8. customPurification by column chromatography (

Sources & evidence

ORD record
ord-0b222eebbe0741ab876f91d76b7f8430
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…