Benzyl Alcohol → HCID 86735353, compound

HRID 839858Notes

Reaction equation

HRID 839858 reaction equation
[C:1]([O:5][C:6](=[O:13])[CH2:7][NH:8][CH2:9][CH2:10][O:11][CH3:12])([CH3:4])(C)C.C(O)[C:15]1[CH:20]=[CH:19]C=[CH:17][CH:16]=1.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.O>C1C=CC=CC=1>[C:23]1([CH3:33])[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1.[CH2:1]([O:5][C:6](=[O:13])[CH2:7][NH:8][CH2:9][CH2:10][O:11][CH3:12])[C:4]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962Water2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 1892547566116-13-0

Product 1

HCID 86735353HCID 86735353, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 55.8 g of N-(2-methoxyethyl)glycine tert-butyl ester in 200 ml of benzene was added 63.8 g of benzyl alcohol and 72.9 g of p-toluenesulfonic acid monohydrate. The mixture was heated at reflux for 10 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solution was concentrated in vacuo, and to the residue was added 300 ml of dry ethyl ether. After 2 hours at room temperature, the formed precipitate was filtered, washed with dry ethyl ether and then recrystallized from ethyl acetate to yield 99.2 g (85 percent) of N-(2-methoxyethyl)glycine benzyl ester p-toluenesulfonate, M.P. 95°-6° C. The following amino acid benzyl ester p-toluenesulfonate not previously reported in the chemical literature were synthesized by the aforementioned procedure.

Workup

  1. temperatureThe mixture was heated
  2. concentrationAt the end of this period, the solution was concentrated in vacuo
  3. additionto the residue was added 300 ml of dry ethyl ether
  4. filtrationthe formed precipitate was filtered
  5. washwashed with dry ethyl ether
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5932a7640e4c4ae38f82bb7ce8e1e117
Source dataset
uspto-grants-1978_06
Patent number
US04097472

Reaction notes

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