4-Hydroxybenzaldehyde → Dimethyl ((4-hydroxyphenyl)methylene)malonate

HRID 890349Notes

Reaction equation

HRID 890349 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:17][CH3:18])(=[O:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13].C1(C)C=CC=CC=1.N1CCCCC1>C(O)(=O)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:11]([C:10]([O:17][CH3:18])=[O:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 1140TolueneHCID 7943Dimethyl malonateHCID 8082Piperidine

Product 1

HCID 103565Dimethyl ((4-hydroxyphenyl)methylene)malonateYield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 4-hydroxybenzaldehyde (280.9 g), dimethyl malonate (289.2 mL) and toluene (1.12 mL) were successively added acetic acid (13.2 mL) and piperidine (11.4 mL). After dehydration under refluxing at internal temperature of 70° C.–75° C. for about 4 hr, the mixture was cooled to internal temperature of not more than 10° C. and stirred further for 1 hr. The precipitated crystals were collected by filtration and washed with toluene (350 mL) to give the title compound (compound [8]; 523.7 g, yield 96.4%).

Workup

  1. temperatureAfter dehydration under refluxing at internal temperature of 70° C.–75° C. for about 4 hr
  2. temperaturethe mixture was cooled to internal temperature of not more than 10° C.
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with toluene (350 mL)

Sources & evidence

ORD record
ord-97c3258f75f947e8a1e86821318edbec
Source dataset
uspto-grants-2006_02
Patent number
US06995271B2

Reaction notes

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