Benzyl Alcohol → HCID 68912874, compound

HRID 732637Notes

Reaction equation

HRID 732637 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:6][CH2:7][CH2:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])[C:3]([OH:5])=[O:4].[CH2:16](O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:16]([O:11][C:10](=[O:12])[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][CH2:6][C:2]([CH3:15])([CH3:1])[C:3]([OH:5])=[O:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 27331562,2,6,6-Tetramethylpimelic Acid

Product 1

HCID 68912874HCID 68912874, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

At room temperature, 34 mg of p-toluenesulfonic acid was added to a mixture of 4.33 g of 2,2,6,6-tetramethylpimelic acid (mfd. by Tokyo Kasei (TCI), Japan), 4.24 g of benzyl alcohol and 16 ml of toluene. By equipping with a Dean-Stark type dehydration tube, this was stirred for 60Hours while heating under reflux, and then cooled down to room temperature. The insoluble matter was removed by filtration, the filtrate was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (methanol-chloroform) to obtain 2.18 g of 7-(benzyloxy)-2,2,6,6-tetramethyl-7-oxoheptanoic acid as a colorless oily substance. FP: 307.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customThe insoluble matter was removed by filtration
  4. concentrationthe filtrate was concentrated under a reduced pressure
  5. customthe thus obtained residue was purified by a silica gel column chromatography (methanol-chloroform)

Sources & evidence

ORD record
ord-bfcc53a43181462bb460072059f1dc5b
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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