3-(4-HYDROXYMETHYL-PHENYL)-PROPAN-1-OL → 4-(3-Hydroxypropyl)benzaldehyde

HRID 2261437Notes

Reaction equation

HRID 2261437 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1>C(O)C.O=[Mn]=O>[OH:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 112406973-(4-HYDROXYMETHYL-PHENYL)-PROPAN-1-OL

Product 1

HCID 129278124-(3-Hydroxypropyl)benzaldehydeYield 95.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-(4-hydroxymethyl-phenyl)-propan-1-ol (500 mg, 3 mmol) in ethanol (40 mL) is treated with MnO2. The suspension is stirred at 80° C. for 5 h before it is filtered and evaporated to give 4-(3-hydroxy-propyl)-benzaldehyde (470 mg) as a brownish oil; LC-MS: tR=0.71 min; 1H NMR (CDCl3): δ 9.97 (s, 1H), 7.81 (d, J=7.6 Hz, 2H), 7.36 (d, J=7.6 Hz, 2H), 3.69 (t, J=6.1 Hz, 2H), 2.80 (t, J=7.6 Hz, 2H), 1.97-1.85 (m, 2H).

Workup

  1. filtrationis filtered
  2. customevaporated

Sources & evidence

ORD record
ord-dd08521883f243d094be80fbafab3d1e
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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