Methanol → HCID 14748266, compound

HRID 1165252Notes

Reaction equation

HRID 1165252 reaction equation
[OH:1][CH:2]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=1)[CH2:3][C:4]#[C:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH3:25]O>C1(C)C=CC=CC=1>[OH:1][CH:2]([CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:18][CH:19]=1)[CH2:3][C:4]#[C:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:25])=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 14748265HCID 14748265, compound

Product 1

HCID 14748266HCID 14748266, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3 g of 8-hydroxy-9-(4-pentylphenoxy)-5-nonynoic acid, the product of Example 7b, 40 ml of MeOH, 40 ml of toluene and 3 drops of BF3 ·Et2O was heated for 12 hr to reflux with a Dean Stark trap to remove water. Solvent was removed and the residue was dissolved in Et2O and was washed NaHCO3 solution and NaCl solution. The ether solution was dried over MgSO4 and removed solvent to give the title compound, an oil.

Workup

  1. temperatureto reflux with a Dean Stark trap
  2. customto remove water
  3. customSolvent was removed
  4. dissolutionthe residue was dissolved in Et2O
  5. washwas washed NaHCO3 solution and NaCl solution
  6. dry with materialThe ether solution was dried over MgSO4
  7. customremoved solvent

Sources & evidence

ORD record
ord-51adfd0caf4748f1a9c38b54690c68c0
Source dataset
uspto-grants-1990_03
Patent number
US04908384

Reaction notes

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