Dichloromethane → 3-Methylthio4-n-propoxy-5-benzyloxybenzaldehyde

HRID 1196692Notes

Reaction equation

HRID 1196692 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]=1[OH:11])[CH:6]=[O:7].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH2:28][CH3:29].C(Cl)Cl>CN(C=O)C.O>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]=1[O:11][CH2:27][CH2:28][CH3:29])[CH:6]=[O:7]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 117781083-Methylthio-4-hydroxy-5-benzyloxybenzaldehyde

Product 1

HCID 104710223-Methylthio4-n-propoxy-5-benzyloxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

64.5 g of 3-methylthio-4-hydroxy-5-benzyloxybenzaldehyde dissolved in a 75 mL of DMF was treated with 50 g of K2CO3 and 32 g of 1-bromopropane and stirred overnight at 70° C. The next day about 1.5 liters of methylene chloride and an equal amount of water was added to the reaction mixture. The organic layer was removed, washed three times with distilled water, dried over MgSO4 and evaporated to yield the title compound as viscous liquid that solidified slowly: NMR (200 MHz, CDCl3) δ 1.02 (t, CH2CH2CH3), 1.82 (m, CH2CH2CH3), 2.48 (s, SCH3), 4.12 (t, OCH2CH3), 5.18 (s, OCH2Ar), 7.26-7.52 (m, ArH), 9.86 (s, ArCHO).

Workup

  1. customThe organic layer was removed
  2. washwashed three times with distilled water
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-f942f9bc83db40faae6215a6b21ca956
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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