Trifluoroacetic acid → (4-(Benzyloxy)phenyl)methanol

HRID 1954443Notes

Reaction equation

HRID 1954443 reaction equation
[CH2:1]([CH:3]([CH2:7][CH3:8])[C:4](O)=[O:5])[CH3:2].[C:9]1(=[O:22])N(CC=O)C(=O)[C:11]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:10]12.F[C:24](F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH:19]1[CH:20]=[CH:21][C:10]([CH2:9][O:22][C:24]2[CH:8]=[CH:7][C:3]([CH2:4][OH:5])=[CH:1][CH:2]=2)=[CH:11][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23297024HCID 23297024, compound

Product 1

HCID 70043(4-(Benzyloxy)phenyl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Phthalimidoacetaldehyde diethylacetate (5.3 g, 20 mmole) was dissolved in chloroform (100 mL) and a trifluoroacetic acid solution (50% aqueous, 80 mL) was added. The reaction mixture was stirred at room temperature for 12 hours. The chloroform layer was collected and dried over sodium sulfate. The filtrate was concentrated to give 3.75 g of the title compound (99% yield): TLC (Rf: 0.4; 40% EtOAc/Hexane), 1H NMR (DMSO-d6) δ 4.6 (s, 2 H, CH2), 7.8 (m, 4 H, Ar), 9.6 (s, 1 H, CHO). 13C NMR (DMSO-d6): δ 47.4 (CH2), 123.4 (Ar), 131.5 (Ar), 134.8 (Ar), 167.3 (CO), 196.8 (CHO).

Workup

  1. customThe chloroform layer was collected
  2. dry with materialdried over sodium sulfate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-14333b4f5cf548529d5135070ccceb7d
Source dataset
uspto-grants-2000_09
Patent number
US06121433

Reaction notes

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