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

HRID 1110820Notes

Reaction equation

HRID 1110820 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-5-benzyloxy-4-hydroxybenzaldehyde 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, 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

Sources & evidence

ORD record
ord-6aa3bf412c61401bb4d4f50261ca8339
Source dataset
uspto-grants-1990_12
Patent number
US04977146

Reaction notes

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