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

HRID 1278937Notes

Reaction equation

HRID 1278937 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-c97f958dbf454f4eaf4ab2b6f974c56a
Source dataset
uspto-grants-2002_09
Patent number
US06444827B1

Reaction notes

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