Trimethylhydroquinone → Chroman

HRID 1248366Notes

Reaction equation

HRID 1248366 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13](O)=[CH:12][CH:11]=1)(=O)[C:2]1[CH:7]=CC=CC=1.C(OC1C=CC(O)=C(C)C=1)(=O)C.CC1C(O)=C(C)C(C)=C(C=1)O>>[O:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:7][CH2:2][CH2:1]1

Participants

4

Reactant 3

HCID 12785TrimethylhydroquinoneHCID 75549p-Hydroxyphenyl benzoateHCID 155324474-Hydroxy-3-methylphenyl acetate

Product 1

HCID 136319Chroman

Procedure

The same reaction and isolation procedures as Synthesis Example 22 were followed except that 4.28 g of 4-benzoyloxyphenol or 3.32 g of 4-acetoxy-2-methylphenol was used in lieu of 3.04 g of trimethylhydroquinone to give the corresponding 3,4-dihydro-2H-benzopyran derivatives. The yield and FD mass spectrum of each product are given in Table 4.

Workup

  1. customThe same reaction and isolation procedures
  2. customas Synthesis Example 22

Sources & evidence

ORD record
ord-fc31969e0f654d27aa30699c2a3cc9fb
Source dataset
uspto-grants-1985_06
Patent number
US04523024

Reaction notes

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