Diethyl Ether → Methyl 5-chloro-2-formylbenzoate

HRID 2170754Notes

Reaction equation

HRID 2170754 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:11]=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13]([O-])([O-])=O.[K+].[K+].CI.CCOCC>CN(C=O)C>[CH3:13][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71762095-Chloro-2-formylbenzoic acid

Product 1

HCID 58437623Methyl 5-chloro-2-formylbenzoateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a heterogeneous mixture of 5-chloro-2-formyl-benzoic acid (1.0 g, 5.42 mmol) and K2CO3 (1.12 g, 8.13 mmol) in DMF (7 ml) was added MeI (0.41 ml, 6.5 mmol) at RT. The reaction mixture was stirred for 4 h then diluted into Et2O and washed with water (2×). The organic layer was dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (700 mg, 3.52 mmol, 65%) as a light yellow solid, which was used without further purification. HPLC: AtRet=1.84 min; LC-MS: m/z 199.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 3.91 (s, 3H), 7.84-7.94 (m, 3H), 10.33 (s, 1H).

Workup

  1. washwashed with water (2×)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4a65d71363bf4d9e95332fd8d83d18cd
Source dataset
uspto-grants-2015_06
Patent number
US09051279B2

Reaction notes

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