Benzene → HCID 22420297, compound

HRID 1720108Notes

Reaction equation

HRID 1720108 reaction equation
[C:1]1([C:3]([CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:15])O)=[CH:4][C:5](=[CH:7][CH:8]=1)O)[OH:2].C1C=CC=CC=1.C1(C)C=CC=CC=1>C1CCCCC1>[O:2]1[C:1]2[C:3](=[CH:4][CH:5]=[CH:7][CH:8]=2)[CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][OH:15]

Participants

5

Reactant 3

HCID 241BenzeneHCID 1140TolueneHCID 22420294HCID 22420294, compound

Product 1

HCID 22420297HCID 22420297, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

The hydroquinonepentanediol compound (19) is refluxed in a nonpolar organic solvent (for example, benzene, toluene, or cyclohexane) in the presence of an alkyl or phenylsulfonic acid (for example, p-toluenesulfonic acid) to cause an intramolecular dehydrocondensation, and then cyclization, whereby the chroman ethanol compound (110) is obtained while retaining the chirality. Accordingly, the configuration of the chiral central carbon atom stemming from the starting mevalonolactone (12) is introduced into the 2-position of the chroman ring. The purification is carried out by silica gel column chromatography.

Sources & evidence

ORD record
ord-16a5b64bc56c4a198f3f94ae2c5d26ab
Source dataset
uspto-grants-1996_04
Patent number
US05504219

Reaction notes

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