Formaldehyde → Chroman

HRID 1434907Notes

Reaction equation

HRID 1434907 reaction equation
OC1C=CC(O)=C(C)C=1C.C=O.C(OC)(=O)C(C)=C.O[C:21]1[CH:22]=[C:23]2[C:28](=[C:29](C)[C:30]=1C)[O:27][C:26](C)(C(OC)=O)[CH2:25][CH2:24]2>>[O:27]1[C:28]2[C:23](=[CH:22][CH:21]=[CH:30][CH:29]=2)[CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6658Methyl MethacrylateHCID 691002,3-DimethylhydroquinoneHCID 23149425HCID 23149425, compound

Product 1

HCID 136319Chroman

Procedure

Into a 30-mL stainless-steel pressure reactor equipped with a stirrer, 1,4-dihydroxy-2,3-dimethylbenzene (0.91 g, 6.6 mmol), an aqueous formalin solution (0.73 g, formaldehyde 37 wt. %, methanol 7 wt. %, and water 56 wt. %), and methyl methacrylate (8.3 g, 83.0 mmol) were placed. The mixture was allowed to react at 180° C. for three hours under stirring, while the reactor was tightly closed. After cooling, the reaction mixture was analyzed, and methyl 6-hydroxy-2,7,8-trimethylchroman-2-carboxylate was found to be formed as a chroman compound. Reaction scores on the basis of 1,4-dihydroxy-2,3-dimethylbenzene 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. temperatureAfter cooling

Sources & evidence

ORD record
ord-d15aa7eaafb24321a4999496ad435f9e
Source dataset
uspto-grants-2009_11
Patent number
US07615650B2

Reaction notes

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