Benzyl Alcohol → HCID 86735353, compound

HRID 1833579Notes

Reaction equation

HRID 1833579 reaction equation
[C:1]([O:5][C:6](=O)[CH2:7][NH:8][CH2:9][CH2:10][O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[C:23]1(C)[C:24]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25]C=CC=1.O>C1C=CC=CC=1>[C:1]1([CH3:2])[CH:3]=[CH:25][C:24]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:23][CH:4]=1.[CH2:14]([O:21][C:6](=[O:5])[CH2:7][NH:8][CH2:9][CH2:10][O:11][CH3:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962Water2×HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 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 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.

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-fd31a4f0451e4675b20c9c08ff3f1834
Source dataset
uspto-grants-1978_01
Patent number
US04066773

Reaction notes

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