Hydrochloric Acid → HCID 86679291, compound

HRID 1519732Notes

Reaction equation

HRID 1519732 reaction equation
[OH-].[Na+].CO.C[O:6][C:7](=[O:26])[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15]/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=2)=[CH:10][CH:9]=1.Cl>O.O1CCOCC1>[CH:24]([C:21]1[CH:20]=[CH:19][C:18](/[CH:17]=[CH:16]/[C:15]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([C:7]([OH:26])=[O:6])=[CH:13][CH:12]=2)=[CH:23][CH:22]=1)=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 86679290HCID 86679290, compound

Product 1

HCID 86679291HCID 86679291, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 20% aqueous solution (1.5 mL) of sodium hydroxide was added to a methanol (20 mL)-1,4-dioxane (20 mL) solution of 4-[(E)-4-(4-formylphenyl)but-3-en-1-yn-1-yl)benzoic acid methyl ester (0.59 g) as obtained in Example 23-(1), and then the mixture was stirred for 3 hours at room temperature. A 20% aqueous solution (1.5 mL) of sodium hydroxide was added, and the mixture was stirred for 30 minutes at room temperature. Water was added, and the mixture was adjusted to pH 3 with 12 mol/L hydrochloric acid. The precipitate was filtered off to obtain 4-[(E)-4-(4-formylphenyl)but-3-en-1-yn-1-yl)benzoic acid (orange solid) (0.55 g, 98%).

Workup

  1. customas obtained in Example 23-(1)
  2. stirringthe mixture was stirred for 30 minutes at room temperature
  3. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-ba2491871de847b7ba8a6db52c729265
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

Loading…