88416-58-4 → 4-(2-Hydroxypropan-2-yl)benzaldehyde

HRID 2060596Notes

Reaction equation

HRID 2060596 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1>C(OCC)(=O)C.ClCCl.O=[Mn]=O>[OH:12][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 1

HCID 1367857388416-58-4

Product 1

HCID 104195204-(2-Hydroxypropan-2-yl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[4-(Hydroxymethyl)phenyl]propan-2-ol (1.0 g, 6 mmol) was dissolved in the mixture of ethyl acetate (10 mL) and dichloromethane (5 mL). To the solution, MnO2 (2.6 g, 30 mmol) was added, and the mixture was stirred overnight at room temperature. The solid was filtered off and washed with ethyl acetate. The combined organic phases were concentrated to afford the title compound. 1H NMR (400 MHz CDCl3): δ 10.00 (s, 1H), 7.80 (d, 2H), 7.60 (d, 2H), 1.60 (s, 6H).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe combined organic phases were concentrated

Sources & evidence

ORD record
ord-656c0edb794d41698126c70cd4528d6a
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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