Hydrochloric Acid → 1-[3,3-Di(ethoxycarbonyl)propyl]-4-methoxymethylbenzene

HRID 1982242Notes

Reaction equation

HRID 1982242 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].[CH3:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23]Br)=[CH:18][CH:17]=1.Cl>CO>[CH2:10]([O:9][C:1]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][CH3:13])=[CH:17][CH:18]=1)=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5360545SodiumHCID 201974281-(2-Bromoethyl)-4-(methoxymethyl)benzene

Product 1

HCID 201976021-[3,3-Di(ethoxycarbonyl)propyl]-4-methoxymethylbenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diethyl malonate (0.32 g) is added to a solution of 0.05 g sodium in 10 ml of methanol. The 1-(methoxymethyl)-4-(2-bromoethyl)benzene (13) (0.5 g) is then added and allowed to react for 8 h. The solution is neutralized with methanolic HCl and is extracted with ether. The ether extract is dried over Na2SO4, and evaporated to yield 1-[3,3-di(ethoxycarbonyl)propyl]-4-methoxymethylbenzene (14). The methyl group is removed by treatment with aqueous HBr in acetic acid, followed by neutralization with aqueous NaOH and extraction with ether. The ether extract is dried over Na2SO4, and evaporated to yield 1-[3,3-di(ethoxycarbonyl)propyl]-4-hydroxymethylbenzene (4).

Workup

  1. customto react for 8 h
  2. extractionis extracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-8a865185406345d196afb0df92b2a7c3
Source dataset
uspto-grants-1986_06
Patent number
US04595690

Reaction notes

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