1-(Phenylmethyl) butanedioate → Butanedioic acid, chloromethyl phenylmethyl ester

HRID 489000Notes

Reaction equation

HRID 489000 reaction equation
[CH2:1]([O:8][C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:34][CH2:35]I>O1CCOCC1>[Cl:34][CH2:35][O:13][C:12](=[O:14])[CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15]

Participants

5

Reactant 3

HCID 87881-(Phenylmethyl) butanedioateHCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 10801108Butanedioic acid, chloromethyl phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Succinic acid monobenzyl ester (4.16 g, 20 mmole) was dissolved in dioxane (20 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 11.6 ml, 18 mmole). The solution was dried in vacuo and coevaporated with toluene several times. The residue was dissolved in methylene chloride (60 ml) and then chloroiodomethane (14.5 ml, 200 mmole) was added to the solution. The reaction solution was stirred for 18 hr and then evaporated and the product was isolated with silica gel column chromatography. 3.64 g

Workup

  1. customThe solution was dried in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride (60 ml)
  3. customevaporated
  4. customthe product was isolated with silica gel column chromatography

Sources & evidence

ORD record
ord-3fa9c7eeaad84eba9cefb08f5d4cd58f
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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