tert-Butyl 4-(hydroxymethyl)phenethylcarbamate → tert-Butyl [2-(4-formylphenyl)ethyl]carbamate

HRID 8911Notes

Reaction equation

HRID 8911 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22337080tert-Butyl 4-(hydroxymethyl)phenethylcarbamate

Product 1

HCID 17796625tert-Butyl [2-(4-formylphenyl)ethyl]carbamateYield 88%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol from above (200 mg, 0.796 mmol) in CH2Cl2 (8 mL) was added activated MnO2 (814 mg, 7.96 mmol) and the mixture stirred at room temperature for 69 h. The reaction mixture was filtered through Celite and the cake was washed with CH2Cl2. The solvent was removed from the filtrate under reduced pressure to give the desired aldehyde as colourless crystals (175 mg, 88%). 1H NMR (CDCl3) δ 1.43 (s, 9H), 2.89 (m, 2H), 3.41 (m, 2H), 4.55 (br s, 1H), 7.37 (d, 2H, J=8.1 Hz), 7.83 (d, 2H, J=7.8 Hz), 9.99 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe cake was washed with CH2Cl2
  3. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-0c5eddc74ce24887a0ef1b770b8df69b
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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