HCID 69977092, compound → HCID 18424530, compound

HRID 1282406Notes

Reaction equation

HRID 1282406 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH:11]=[CH:12][C:13]([O:15][CH3:16])=[O:14])[CH:3]=1.ClC1C=CC(C(O)=O)=C(C=CC(O)=O)C=1>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:3]=1

Participants

3

Reactant 2

HCID 69977092HCID 69977092, compound2×HCID 69977541HCID 69977541, compound

Product 1

HCID 18424530HCID 18424530, compound

Procedure

Without addition of an additional hydrogenation catalyst, 43 g of 4-chloro-2-(3-hydroxy-3-oxo-1-propenyl)-benzoic acid in the form of the isolated solid from Example 5 in 400 ml of methanol are hydrogenated at 40° C. and a hydrogen pressure of from 20 to 40 bar. Filtration through Celite® and removal of the solvents under reduced pressure gives 35.3 g of product which, according to gas chromatography, contains 81 % of 4-chloro-2-(3-methoxy-3-oxo-1-propenyl)-benzoic acid. The same product is obtained using, instead of 4-chloro-2-(3-hydroxy-3-oxo-1-propenyl)-benzoic acid, 4-chloro-2-(3-methoxy-3-oxo-1-propenyl)-benzoic acid.

Workup

  1. customThe same product is obtained

Sources & evidence

ORD record
ord-0096cab94c9a40f6938466204274a66e
Source dataset
uspto-grants-2002_09
Patent number
US06455725B1

Reaction notes

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