Potassium Carbonate → Methyl 4-(cyclopropylmethoxy)-3-formylbenzoate

HRID 1776570Notes

Reaction equation

HRID 1776570 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH:22]1[CH2:24][CH2:23]1>CN(C=O)C>[CH:22]1([CH2:21][O:13][C:12]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[CH:1]=[O:2])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl ester

Product 1

HCID 86679526Methyl 4-(cyclopropylmethoxy)-3-formylbenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-formyl-4-hydroxybenzoate (2 g, 11.10 mmol) in DMF (20 ml), K2CO3 (3.07 mg, 22.2 mmol) and (bromomethyl)cyclopropane (2.156 ml, 22.2 mmol) were added. The mixture was stirred at RT for 2 hours. The reaction was quenched with water, and the product was extracted with EtOAc. The organic layer was washed with water (2×) and NaCl sat. sol., dried over Na2SO4 and evaporated under vacuum to give 2.6 g of the desired compound (quantitative yield).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe product was extracted with EtOAc
  3. washThe organic layer was washed with water (2×) and NaCl sat. sol.
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-ca236f6f03274621bcc470c04d30c5d4
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…