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

HRID 1085811Notes

Reaction equation

HRID 1085811 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

Procedure

64.5 g of 3-Methylthio-4-hydroxy-5benzyloxybenzaldehyde 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°. 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 a 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, OCH2CH2CH3), 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 to a 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, OCH2CH2CH3), 5.18(s, OCH2Ar), 7.26-7.52(m, ArH), 9.86(s, ArCHO)

Sources & evidence

ORD record
ord-35ca6332d19047ec8657643ecd62aa61
Source dataset
uspto-grants-1991_04
Patent number
US05011847

Reaction notes

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