Benzyl Alcohol → HCID 10662990, compound

HRID 2392973Notes

Reaction equation

HRID 2392973 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[C:10]1([CH3:20])[C:11](S(O)(=O)=O)=[CH:12][CH:13]=[CH:14][CH:15]=1.[CH2:21](O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C)C(S([O-])(=O)=O)=CC=CC=1>C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C.CCOCC.O>[NH:1]([CH2:6][C:7]([O:9][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:8])[CH2:2][C:3]([O:5][CH2:20][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:4]

Participants

10

Reactant 4

HCID 244Benzyl AlcoholHCID 69252-Methylbenzenesulfonic acidHCID 8897Iminodiacetic acidHCID 3424274Toluenesulfonate2×

Product 1

HCID 10662990HCID 10662990, compoundYield 91%

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of iminodiacetic acid (16.64 g, 0.125 mol), toluenesulfonic acid (28.5 g, 0.15 mol), and 60 ml of benzyl alcohol in 100 ml benzene was refluxed for 24 h with continuous removal of water using a Dean-Stark trap. After addition of ether to the cooled reaction mixture, toluenesulfonate salt of the benzylated iminodiacetate was obtained as a solid. Subsequently, triethylamine (25 ml) was added to a suspension of the toluenesulfonate salt in ethyl acetate and stirred for 30 minutes. The ethyl acetate solution was washed with water, dried with MgSO4, filtered and concentrated under reduced pressure affording 35.7 g (91%) of compound 1 used for the next reaction step without further purification. NMR (CDCl3):1.4-2.2 (br s,1H), 3.52 (s,4H), 7.35 (s,10H).

Workup

  1. customwas obtained as a solid
  2. washThe ethyl acetate solution was washed with water
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-003240843bf74abc9640963d56593161
Source dataset
uspto-grants-1998_09
Patent number
US05804164

Reaction notes

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