HCID 86691648, compound → HCID 86691647, compound

HRID 2204032Notes

Reaction equation

HRID 2204032 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 86691648HCID 86691648, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86691647HCID 86691647, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl 2-(12-hydroxydodecyl)malonate (3.91 g, 11.35 mmol) was dissolved in dry DCM (60 ml), then PCC (3.67 g, 17.025 mmol) was added portion-wise to it at 0° C. The reaction was allowed to warm to room temperature and stirring was continued for another 3 h. The reaction mixture was concentrated under reduced pressure and purified by silica gel column (8% EtOAc in Hexane) to give diethyl 2-(12-oxododecyl)malonate (2.84 g, 73%) as a colorless liquid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by silica gel column (8% EtOAc in Hexane)

Sources & evidence

ORD record
ord-88be20a5ec9d42dca2612b09218c93a7
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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