Tetrahydrofuran → HCID 86679261, compound

HRID 1519686Notes

Reaction equation

HRID 1519686 reaction equation
[OH-].[Na+].C1COCC1.[CH3:8][O:9][CH:10]([O:30][CH3:31])[C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]2[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=2)=[CH:13][CH:12]=1>CO>[CH3:31][O:30][CH:10]([O:9][CH3:8])[C:11]1[CH:12]=[CH:13][C:14]([C:17]#[C:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86679260HCID 86679260, compound

Product 1

HCID 86679261HCID 86679261, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2.0 mol/L sodium hydroxide aqueous solution (0.10 L) was added to a THF (0.25 L)-methanol (0.25 L) solution of ethyl 4-{[4-(dimethoxymethyl)phenyl]ethynyl}benzoate (21 g) as obtained in Example 10-(2), and the mixture was stirred for 3 hours at room temperature. The solvent was distilled off, and then water and acetic acid were added to the residue to adjust it to pH 4. The precipitate was filtered off and dried. Hexane/ethyl acetate (3:1 (v/v)) was added, and the mixture was stirred for a while. The precipitate was filtered off and dried to obtain 4-{[4-(dimethoxymethyl)phenyl]ethynyl}benzoic acid (white solid) (15 g, 75%).

Workup

  1. customas obtained in Example 10-(2)
  2. distillationThe solvent was distilled off
  3. additionwater and acetic acid were added to the residue
  4. filtrationThe precipitate was filtered off
  5. customdried
  6. additionHexane/ethyl acetate (3:1 (v/v)) was added
  7. stirringthe mixture was stirred for a while
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-3bfc1e1954ba4ff6a1c86dedc728fb51
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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