Hydrochloric Acid → HCID 70578051, compound

HRID 225305

Reaction equation

HRID 225305 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[ClH:13].[CH2:14]=O>CO>[ClH:13].[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH2:14][Cl:13])[CH:7]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 921434-Hydroxyphenylglycine

Product 1

HCID 70578051HCID 70578051, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (-)-α-amino-4-hydroxybenzeneacetic acid (100 g, 0.6 mole) in a minimum amount of concentrated hydrochloric acid at 35°-40° C. is added 50 ml of aqueous formaldehyde (35-37%) (0.6 mole). The addition of hydrogen chloride gas is begun. After 5-10 minutes, a solid begins to precipitate. Stirring is continued for 30 minutes, and the solid is then collected. The crude product is washed with ether and with acetone. A second crop is obtained from the filtrate after standing at room temperature overnight. Total yield is 102 g (67%) m.p. >300° C., [α]D18 =-134° (c 4.75, CH3OH) NMR (DMSO-D6) ppm (δ) 4.68 (s,2), 4.9 (broad s,1), 6.9-7.6 (superimposed q and s,3).

Workup

  1. customto precipitate
  2. waitis continued for 30 minutes
  3. customthe solid is then collected
  4. washThe crude product is washed with ether and with acetone
  5. customA second crop is obtained from the filtrate
  6. waitafter standing at room temperature overnight

Sources & evidence

ORD record
ord-5af12cd787af44039489c0a8ab470093
Source dataset
uspto-grants-1980_11
Patent number
US04236002

Linked notes

Loading…