Benzene → HCID 22420297, compound

HRID 257616Notes

Reaction equation

HRID 257616 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-e30b7575dab74c2480879321916ba924
Source dataset
uspto-grants-1993_11
Patent number
US05262552

Reaction notes

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