Formaldehyde → HCID 10171518, compound

HRID 659756Notes

Reaction equation

HRID 659756 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]>>[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

4

Reactant 3

HCID 712FormaldehydeHCID 6658Methyl MethacrylateHCID 12785Trimethylhydroquinone

Product 1

HCID 10171518HCID 10171518, compoundYield 72.6%

Conditions

Temperature
40 °C

Procedure

In a 1 L stainless-steel autoclave, 100 g (0.657 mol) of 1,4-dihydroxy-2,3,5-trimethylbenzene, 110 g of an aqueous formalin solution (formaldehyde 37 wt %, water 56 wt %, and methanol 7 wt %), and 330 g (3.296 mol) of methyl methacrylate were placed. The mixture was allowed to react at 180° C. for 3 hours under stirring. After the mixture was cooled to 40° C., precipitated crystals were filtered, and rinsed twice with 200 g of methanol. The collected crystals were dried to obtain the aimed methyl 6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylate (hereinafter, referred to as CCM) in an amount of 135 g (0.478 mol as CCM, yield: 72.6%, chemical purity: 93.5%).

Workup

  1. customto react at 180° C. for 3 hours
  2. customprecipitated crystals
  3. filtrationwere filtered
  4. washrinsed twice with 200 g of methanol
  5. customThe collected crystals were dried

Sources & evidence

ORD record
ord-6188756b52024f68825017f8ca0a65aa
Source dataset
uspto-grants-2011_12
Patent number
US08080676B2

Reaction notes

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