Formaldehyde → HCID 18008635, compound

HRID 987361Notes

Reaction equation

HRID 987361 reaction equation
[CH2:1]([C:10]1[CH:11]=[C:12]([CH3:17])[C:13]([OH:16])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH2:18]=[O:19]>CC1C=CC(O)=CC=1.CC1C=CC(O)=CC=1.CC1C=CC(O)=CC=1.CC1C=CC(O)=CC=1.[Ti].C1(C)C=CC=CC=1>[CH3:17][C:12]1[CH:11]=[C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:15]=[C:14]([CH:18]=[O:19])[C:13]=1[OH:16]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 844264-Nonyl-o-cresol

Product 1

HCID 18008635HCID 18008635, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 11465691HCID 11465691, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
215 °C

Procedure

To toluene (500 mL) in a 2-I Parr pressure reactor at 220° C. was added a slurry of 4-nonyl-2-cresol (1a) (234 g, 1 mol), titanium(IV) cresylate (2 mL) and powder paraformaldehyde (83 g, 2.8 mol) for 10 mins. maintaining the temperature at 210-220° C. The reaction was kept for additional 20 mins. Crude product was collected in an expansion tank and the residue in the pressure reactor washed with toluene (200-mL×2). Combined toluene phases were concentrated in vacuo. The resulting viscous dark amber liquid was distilled in vacuo to obtain 3-methyl-5-nonylsalicylaldehyde (183 g) in 70% yield.

Workup

  1. customCrude product was collected in an expansion tank
  2. washthe residue in the pressure reactor washed with toluene (200-mL×2)
  3. concentrationCombined toluene phases were concentrated in vacuo
  4. distillationThe resulting viscous dark amber liquid was distilled in vacuo

Sources & evidence

ORD record
ord-287a2c503bae49599fca550ec0901801
Source dataset
uspto-grants-2003_10
Patent number
US06632410B2

Reaction notes

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