O-Cresol → HCID 15657729, compound

HRID 1646619Notes

Reaction equation

HRID 1646619 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]=1.[CH2:14]=[CH:15][CH:16]=[CH2:17].OC1C=CC=CC=1C>C1(C)C=CC=CC=1>[CH2:14]1[C@@H:2]2[C@@:1]([C:11]([OH:13])=[O:12])([C:10]3[C:5]([CH2:4][CH2:3]2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:17][CH:16]=[CH:15]1

Participants

5

Reactant 3

HCID 335O-CresolHCID 78451,3-ButadieneHCID 5823771-Naphthalenecarboxylic acid, 3,4-dihydro-

Product 1

HCID 15657729HCID 15657729, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,4-dihydronaphthalene-1-carboxylic acid (29.7 g) in toluene (75 ml) was added butadiene (16 g) and a trace of butyrated hydroxy toluene (BHT). The solution was heated to 180° for 18 hours in a sealed reactor, then chromatographed twice over silica gel. Recrystallization from ethyl acetate/heptane affords the title compound as a colorless crystalline solid (10.5 g). The recovered starting material was rereacted with butadiene to afford, after workup, additional title product (8.0 g). ##STR19##

Workup

  1. temperatureThe solution was heated to 180° for 18 hours in a sealed reactor
  2. customchromatographed twice over silica gel
  3. customRecrystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-4698de96f9d94fd1bb3b7c7be48803c7
Source dataset
uspto-grants-1993_01
Patent number
US05180736

Reaction notes

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