Formaldehyde → HCID 10171518, compound

HRID 1434906Notes

Reaction equation

HRID 1434906 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].[CH2:12]=O.[C:14]([O:19][CH3:20])(=[O:18])[C:15]([CH3:17])=[CH2:16].O>CO>[OH:1][C:2]1[C:7]([CH3:12])=[C:6]2[C:5](=[C:4]([CH3:10])[C:3]=1[CH3:11])[O:9][C:15]([CH3:17])([C:14]([O:19][CH3:20])=[O:18])[CH2:16][CH2:8]2

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 6658Methyl MethacrylateHCID 12785Trimethylhydroquinone2×

Product 1

HCID 10171518HCID 10171518, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 30-mL stainless-steel pressure reactor equipped with a stirrer, 1,4-dihydroxy-2,3,5-trimethylbenzene (1.0 g, 6.6. mmol), paraformaldehyde (0.4 g, 13.2 mmol), methyl methacrylate (3.3 g, 32.9 mmol), and water (0.29 g, 16.1 mmol) were placed. The mixture was allowed to react at 180° C. for three hours under stirring, while the reactor was tightly closed. After completion of reaction, the reaction mixture was cooled to room temperature, and methanol was added to the mixture, whereby crystals were precipitated. The crystals were collected through filtration, to thereby yield methyl 6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylate in the form of white powder (1.3 g, 4.9 mmol). Reaction scores on the basis of 1,4-dihydroxy-2,3,5-trimethylbenzene and chemical purity which was determined through HPLC were found to be as follows:

Workup

  1. customInto a 30-mL stainless-steel pressure reactor equipped with a stirrer
  2. customto react at 180° C. for three hours
  3. customwas tightly closed
  4. customAfter completion of reaction
  5. customwere precipitated
  6. filtrationThe crystals were collected through filtration

Sources & evidence

ORD record
ord-ba88e713221d4d85ae197b2a03078515
Source dataset
uspto-grants-2009_11
Patent number
US07615650B2

Reaction notes

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