Hydrochloric Acid → HCID 19009345, compound

HRID 2398969Notes

Reaction equation

HRID 2398969 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[OH-].[NH4+:15].Cl>O>[CH3:6][C:7]1[CH:12]=[C:11]([CH:2]([C:1]([OH:5])=[O:4])[NH2:15])[CH:10]=[CH:9][C:8]=1[OH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 335O-CresolHCID 760Glyoxylic AcidHCID 14923Ammonium Hydroxide

Product 1

HCID 19009345HCID 19009345, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 59.02 g. (0.6 mole) of 75% glyoxylic acid in 100 ml. of water was added to a suspension of 54.6 g. (0.5 mole) of 2-methylphenol and 140 ml. of conc. ammonium hydroxide in 400 ml. of water at room temperature. The temperature of the mixture rose to 37° C. The mixture was stirred at room temperature for 65 hours. The solution, initially at pH 10.1, was adjusted to pH 6.8 with 6 N hydrochloric acid causing the product to crystallize. The product was collected by filtration, washed with water and dried in vacuo over phosphorus pentoxide giving 31.5 g. (34.8%) of 2-(3'-methyl-4'-hydroxyphenyl)glycine; decomp. 196°-199° C. The infrared and nuclear magnetic resonance spectra were consistent for the desired product. Reference: Belgium Pat. No. 774,029 to Beecham Group Limited, 1972 (Farmdoc 27, 122T) which reports m.p. 205°-207° C. Anal. Calcd. for C9H11NO3 : C, 59.66; H, 6.13; N, 7.73. Found: C, 57.68; H 6.23; N, 7.47; H2O, 2.34 Found, corrected for 2.34% H2O: C, 59.06; H, 6.12; N, 7.67.

Workup

  1. customat room temperature
  2. customrose to 37° C
  3. customto crystallize
  4. filtrationThe product was collected by filtration
  5. washwashed with water
  6. dry with materialdried in vacuo over phosphorus pentoxide giving 31.5 g
  7. custom196°-199° C

Sources & evidence

ORD record
ord-9b552ae8d6fa42d1aaa47f7a7ca09c7e
Source dataset
uspto-grants-1977_05
Patent number
US04026888

Reaction notes

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