Mesitylene → 5-Allyl-6-chloroindan-4-ol

HRID 13945

Reaction equation

C([O:4][C:5]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][CH2:9]2)C=C.[C:15]1(C)[CH:20]=C(C)C=C(C)[CH:16]=1>>[CH2:20]([C:13]1[C:12]([Cl:14])=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][C:6]=2[C:5]=1[OH:4])[CH:15]=[CH2:16]

Participants

Reactant 2

HCID 7947Mesitylene

HCID 685839704-(Allyloxy)-6-chloroindane

Product 1

HCID 685858685-Allyl-6-chloroindan-4-olYield 56%

Procedure

Treatment of 4-(allyloxy)-6-chloroindane (8.0 g, 0.038 mol) in refluxing mesitylene (270 mL) generally according to the procedure described for Intermediate 1 afforded 4.5 g (56%) of 5-allyl-6-chloroindan-4-ol as a colorless oil which solidified into a white solid upon standing. mp 37-39° C.; Anal. calcd. for C12H13ClO.0.1H2O: C, 68.48; H, 6.32. Found: C, 68.54; H, 6.29.

Sources & evidence

ORD record: ord-a22c5adcc1c84f2c827b68d9447ff539
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728155B2

Linked notes

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