2,3-Dimethylbenzaldehyde → HCID 22486840, compound

HRID 1169978Notes

Reaction equation

HRID 1169978 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11]([Li])[CH3:12]>O1CCCC1>[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 342242,3-DimethylbenzaldehydeHCID 178506846HCID 178506846, compound

Product 1

HCID 22486840HCID 22486840, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,3-dimethylbenzaldehyde (1.0 g, 7.5 mmol) in anhydrous tetrahydrofuran (50 ml), at −78° C. and under nitrogen, was added ethyllithium (0.5M in benzene:cyclohexane 9:1, 14.9 ml, 7.5 mmol), dropwise via syringe. The reaction mixture was stirred at −78° C. for 30 min and then poured into ice cold hydrochloric acid (2N, 20 ml). The mixture was extracted with ethyl acetate (2×50 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (1.22 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-540a0c42173145698cc439e0ef2e23b7
Source dataset
uspto-grants-2010_11
Patent number
US07825149B2

Reaction notes

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