4-Hydroxybenzaldehyde → HCID 157607, compound

HRID 1861544Notes

Reaction equation

HRID 1861544 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:16][C:14](=[O:15])[NH:13][C:11]1=[O:12].N1CCCCC1.Cl>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:16]2[NH:10][C:11](=[O:12])[NH:13][C:14]2=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 10006Hydantoin

Product 1

HCID 157607HCID 157607, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-hydroxybenzaldehyde (100 g, 0.819 M), hydantoin (90 g, 0.9 M) and piperidine (165 ml) was heated to 130° C. for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to 60° C. and 3.2 l water was added. The reaction mixture was acidified with 12N HCl. The precipitated solid was filtered and washed with cold water to yield the title compound of the formula (18) (147 g, 88%). (Org Syn. Vol V., pp627).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to 60° C.
  3. filtrationThe precipitated solid was filtered
  4. washwashed with cold water

Sources & evidence

ORD record
ord-2f16b99c67e549318c8fcc7c2d59262f
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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