Hydrochloric Acid → HCID 59300255, compound

HRID 1776561Notes

Reaction equation

HRID 1776561 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.Cl>CN(C=O)C.CCOC(C)=O>[CH:19]1([CH2:18][O:10][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[OH:1])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 59300255HCID 59300255, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3,4-dihydroxybenzaldehyde (0.5 g, 3.62 mmol), K2CO3 (0.550 g, 3.98 mmol) and (bromomethyl)cyclopropane (0.386 ml, 3.98 mmol) in DMF (12 ml) was heated to 50° C. overnight. The reaction mixture was portioned between EtOAc and HCl 1N. The organic phase was washed several times with brine and dried over Na2SO4; the solvent was removed; and the crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=90:10 to 85:15) to give 4-(cyclopropylmethoxy)-3-hydroxybenzaldehyde (0.370 g, 1.925 mmol, 53.2% yield, MS/ESI+ 193.0 [MH]+).

Workup

  1. washThe organic phase was washed several times with brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed
  4. customand the crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=90:10 to 85:15)

Sources & evidence

ORD record
ord-1271c4e773c845eeb26dc78488afa54c
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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