Benzene → 4-(5-Pentyl-1,3-dioxan-2-YL)benzoic acid

HRID 223683Notes

Reaction equation

HRID 223683 reaction equation
[CH2:1]([CH:6]([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH2:3][CH2:4][CH3:5].[C:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([OH:13])=[O:12].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:1]([CH:6]1[CH2:9][O:10][CH:18]([C:17]2[CH:20]=[CH:21][C:14]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=2)[O:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 120884-Formylbenzoic acidHCID 1175092-Pentyl-1,3-propanediol

Product 1

HCID 135612264-(5-Pentyl-1,3-dioxan-2-YL)benzoic acidYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-n-pentylpropane-1,3diol (8 g, 0.054 m), 4-carboxybenzaldehyde (8 g, 0.053 m), benzene (200 ml) and a catalytic amount of 4-toluenesulfonic acid was azeotropically refluxed until no more water was collected. The cold reaction mixture was washed with saturated NaHCO3 solution and water and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was crystallized from ethanol to yield 4-(5-n-pentyl-1,3-dioxan-2-yl) benzoic acid (12 g, 80%)

Workup

  1. customwas collected
  2. customThe cold reaction mixture
  3. washwas washed with saturated NaHCO3 solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-47393453eab443779abc4ab477b5496d
Source dataset
uspto-grants-1982_10
Patent number
US04356104

Reaction notes

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