Formic Acid → 4-(Benzyloxy)-3-ethylphenol

HRID 2245904Notes

Reaction equation

HRID 2245904 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](C=O)=[CH:11][C:10]=1[CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:20].[NH4+].[NH4+].C(O)=O.C(OC(=O)C)(=O)C.P(=O)(O)(O)O.C1(C)C=CC(S(O)(=O)=O)=CC=1.S(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([OH:20])=[CH:11][C:10]=1[CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 7

HCID 284Formic AcidHCID 1004Phosphoric AcidHCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 62648Ammonium PersulfateHCID 21435446HCID 21435446, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 218415034-(Benzyloxy)-3-ethylphenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a reactor were charged 2.50 g (10 mmol) of 4-benzyloxy-3-ethylbenzaldehyde obtained in Step 3, 3.09 g (14 mmol) of ammonium persulfate, 0.96 g (21 mmol) of formic acid, 0.40 g (4.0 mol) of acetic anhydride, and 15 g of toluene, here was added aqueous solution of phosphoric acid dropwise at 60° C., and the mixture was stirred for 20 hours. After the reaction mixture was cooled to ambient temperature, 0.094 g (0.30 mmol) of p-toluenesulfonic acid dissolved in water was added dropwise, and the mixture was stirred for 9 hours. To the reaction mixture, 20 g of saturated aqueous solution of sodium bisulfite was added, and the mixture was stirred for 30 minutes. The organic layer was washed with water, the solvent was evaporated, and the residue was purified by column chromatography (ethyl acetate:hexane=1:10, SiO2) to yield the desired product, 4-benzyloxy-3-ethylphenol, as red liquid (0.92 g, Yield: 39%).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred for 9 hours
  3. stirringthe mixture was stirred for 30 minutes
  4. washThe organic layer was washed with water
  5. customthe solvent was evaporated
  6. customthe residue was purified by column chromatography (ethyl acetate:hexane=1:10, SiO2)

Sources & evidence

ORD record
ord-08b254c731e448839d48ba6eb83f5fca
Source dataset
uspto-grants-2010_03
Patent number
US07683203B2

Reaction notes

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