3-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol → 4-(3-Hydroxy-propyl)-3,5-dimethyl-benzaldehyde

HRID 2240772Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][CH2:11][CH2:12][OH:13])=[C:5]([CH3:14])[CH:4]=1>C(O)C.O=[Mn]=O>[OH:13][CH2:12][CH2:11][CH2:10][C:6]1[C:7]([CH3:9])=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[CH3:14]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propan-1-ol (850 mg, 4.38 mmol) in ethanol (20 mL), MnO2 (1.14 g, 13.1 mmol) is added and the resulting suspension is stirred at 85° C. for 24 h. The mixture is filtered through celite and the solvent of the filtrate is evaporated. The product is purified by CC on silica gel eluting with DCM containing 3% of methanol to give 4-(3-hydroxy-propyl)-3,5-dimethyl-benzaldehyde as a pale yellow solid; LC-MS: tR=0.81 min; 1H NMR (CDCl3): δ 9.89 (s, 1H), 7.51 (s, 2H), 3.76 (t, J=5.8 Hz, 2H), 2.81-2.74 (m, 2H), 2.40 (s, 6H), 1.80-1.68 (m, 2H).

Workup

filtrationThe mixture is filtered through celite
customthe solvent of the filtrate is evaporated
customThe product is purified by CC on silica gel eluting with DCM containing 3% of methanol

Sources & evidence

ORD record: ord-46d07f8f4e7841cfb972f10ee019ed4a
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723378B2

Reaction notes

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