2-Chlorobenzaldehyde → HCID 13557414, compound

HRID 1583713Notes

Reaction equation

HRID 1583713 reaction equation
[C:1]([C@H:5]([C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[OH:8])[OH:6])([O:3][CH3:4])=[O:2].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]1[O:8][C@H:7]([C:9]([O:11][CH3:12])=[O:10])[C@@H:5]([C:1]([O:3][CH3:4])=[O:2])[O:6]1

Participants

5

Reactant 2

HCID 69962-ChlorobenzaldehydeHCID 21142Butanedioic acid, 2,3-dihydroxy-, diMethyl ester, (2R,3R)-rel-

Product 1

HCID 13557414HCID 13557414, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

In this example 50.0 g (0.28 mole) of dimethyl D-tartrate and 39.5 g (0.28 mole) of 2-chlorobenzaldehyde were refluxed for 48 hours in 500 ml of toluene in the presence of 0.2 g of p-toluenesulfonic acid. Water was azeotroped off with the aid of a Dean-Stark trap. The reaction mixture was concentrated by evaporation under reduced pressure to afford 50.8 g (60% yield) of the title compound as a solid which was washed with hexane and ether.

Workup

  1. customWater was azeotroped off with the aid of a Dean-Stark trap
  2. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f9db301a2d5b4a70844b7c345d863078
Source dataset
uspto-grants-1985_11
Patent number
US04554011

Reaction notes

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