Benzyl Alcohol → HCID 53922886, compound

HRID 580805Notes

Reaction equation

HRID 580805 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[C:13]([OH:40])(=[O:39])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37].C(O)C1C=CC=CC=1>C1C=CC=CC=1>[C:13]([O:40][CH2:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:39])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 2724554Tetracosanedioic acid

Product 1

HCID 53922886HCID 53922886, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Toluene-4-sulfonic acid monohydrate (0.05 g, 0.28 mmol) is added to a suspension of tetracosanedioic acid (5.0 g, 80%, 10.03 mmol) in benzene (180 ml). The mixture is heated to 80° C., whereafter benzyl alcohol (1.08 g, 10.03 mmol) in benzene (10 ml) is added dropwise to the resulting solution. The reaction mixture is refluxed for 20 hours and water is removed azeotropically with a Dean Stark trap. The solvent is removed under reduced pressure and the residue washed with petroleum ether. The product is dissolved in refluxing diethyl ether and purified by flash chromatography on a silica column with methylene chloride/methanol (20:1) as eluant to yield the title compound as a white crystalline solid. 13C NMR (75 MHz, CDCl3): δ 24.0, 28.5, 29.7, 30.9, 34.4, 66.2, 128.2, 128.5, 136.0, 174.1, 176.9.

Workup

  1. additionis added dropwise to the resulting solution
  2. temperatureThe reaction mixture is refluxed for 20 hours
  3. customwater is removed azeotropically with a Dean Stark trap
  4. customThe solvent is removed under reduced pressure
  5. washthe residue washed with petroleum ether
  6. dissolutionThe product is dissolved
  7. temperaturein refluxing diethyl ether
  8. custompurified by flash chromatography on a silica column with methylene chloride/methanol (20:1) as eluant

Sources & evidence

ORD record
ord-6717a75fab3c40e99d7a2e2629868139
Source dataset
uspto-grants-1999_07
Patent number
US05919753

Reaction notes

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