Phloroglucinol → 7,8,9,10-Tetrahydro-1,3-dihydroxy-6H-dibenzo[b,d]pyran-6-one

HRID 1835679Notes

Reaction equation

HRID 1835679 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].O=[C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](OCC)=[O:18]>S(=O)(=O)(O)O>[OH:2][C:1]1[C:9]2[C:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:17](=[O:18])[O:8][C:7]=2[CH:6]=[C:4]([OH:5])[CH:3]=1

Participants

4

Reactant 2

HCID 359PhloroglucinolHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 53979347,8,9,10-Tetrahydro-1,3-dihydroxy-6H-dibenzo[b,d]pyran-6-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Phloroglucinol (1 g) and ethyl 2-oxocyclohexane carboxylate (1.32 g) were stirred in 75% sulfuric acid (10 ml) overnight, the mixture poured into ice water and filtered Yield: 1.55 g.

Workup

  1. filtrationfiltered Yield: 1.55 g

Sources & evidence

ORD record
ord-c934044cd1174b769137337dc8356534
Source dataset
uspto-grants-2004_08
Patent number
US06774103B1

Reaction notes

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