Dichloromethane → HCID 15146814, compound

HRID 854946Notes

Reaction equation

[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[CH2:10][OH:11].ClCCl>O1CCCC1.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

Conditions

Temperature: 40 °C

Procedure

The (2-amino-5-chloro-3-methylphenyl)methanol (10.8 g, 63.1 mmol) was dissolved in tetrahydrofuran (20 mL). Dichloromethane (50 mL) was added along with activated carbon (16.3 g). Activated manganese dioxide (16.8 g, 189 mmol) was added and the solution stirred at 40° C. for 16 h. The solution was cooled to room temperature and vacuum filtered through a celite. The solvent was removed at reduced pressure and the 2-amino-5-chloro-3-methylbenzaldehyde (7.90 g, 46.0 mmol) obtained by recrystallization from diethyl ether/hexanes (1:10, 100 mL). HRMS m/z 169.0280; calcd 169.0294.

Workup

temperatureThe solution was cooled to room temperature
filtrationvacuum filtered through a celite
customThe solvent was removed at reduced pressure

Sources & evidence

ORD record: ord-c053bb4c251540a594a93e314bb11973
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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