Benzene → HCID 20243240, compound

HRID 2164346Notes

Reaction equation

HRID 2164346 reaction equation
[C:1]([C:8]1[C:14]([OH:15])=[C:13]([C:16](C(C)C)=[CH2:17])[C:12]([OH:21])=[CH:11][C:9]=1[OH:10])(=[O:7])[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].F[C:23](F)(F)[C:24]([OH:26])=O.[CH:29]1C=CC=CC=1>>[OH:21][C:12]1[CH:11]=[C:9]([OH:10])[C:8]([C:1](=[O:7])[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[C:14]2[C:13]=1[CH2:16][CH2:17][C:24]([CH3:23])([CH3:29])[O:26]2.[OH:15][C:14]1[C:8]([C:1](=[O:7])[CH2:2][CH2:3][CH:4]([CH3:5])[CH3:6])=[C:9]([OH:10])[CH:11]=[C:12]2[C:13]=1[CH2:16][CH2:17][C:24]([CH3:23])([CH3:29])[O:26]2

Participants

5

Reactant 3

HCID 241BenzeneHCID 6422Trifluoroacetic acidHCID 20243235HCID 20243235, compound2×

Product 2

HCID 20243240HCID 20243240, compoundHCID 54187574HCID 54187574, compound

Procedure

2-Isocaproyl-4-(3-methylbuten-2-yl)phloroglucinol (7 (2 g) was suspended in benzene (25 ml). Trifluoro acetic acid (1.5 ml) was added and the mixture was stirred for 6 hours at room temperature. The resulting solution was stripped to dryness under vacuum. The residue was chromatographed, preferably on silica gel (open column chromatography, preparative HPLC or preparative TLC) using preferably mixtures of benzene and ethyl acetate or petroleum ether and ethyl acetate for eluation. Two chromanes, namely 5,7-dihydroxy-2,2-dimethyl-8-isocaproyl chroman (31 and 5,7 -dihydroxy-2,2-dimethyl-6-isocaproyl chroman (33, were obtained in a ratio of about 3 to 2. These chromanes were both recrystallized from petroleum ether to give light straw coloured crystals.

Workup

  1. customThe residue was chromatographed, preferably on silica gel (open column chromatography, preparative HPLC or preparative TLC)

Sources & evidence

ORD record
ord-1ac605a3c9814f809a259555b02cc0d9
Source dataset
uspto-grants-1985_03
Patent number
US04503256

Reaction notes

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