Dodecylbenzenesulphonic acid → 2,3-dimethoxy-7,7-dimethyl-9-trifluoromethyl-7H-benzo[C]fluoren-5-ol

HRID 404856

Reaction equation

HRID 404856 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[C:12]([OH:23])=[CH:11][C:10]=2[C:24]([CH3:27])([CH3:26])O)=[CH:5][CH:4]=1.COC1C=C(C2C3C(=CC(C(F)(F)F)=CC=3)C(O)=CC=2C(C)(C)O)C=CC=1OC.C(C1C=CC=CC=1S(O)(=O)=O)CCCCCCCCCCC>C1(C)C=CC=CC=1>[CH3:20][O:19][C:16]1[C:15]([O:21][CH3:22])=[CH:14][C:13]2[C:12]([OH:23])=[CH:11][C:10]3[C:24]([CH3:27])([CH3:26])[C:5]4[CH:4]=[C:3]([C:2]([F:1])([F:29])[F:28])[CH:8]=[CH:7][C:6]=4[C:9]=3[C:18]=2[CH:17]=1

Participants

5

Reactant 3

HCID 25457Dodecylbenzenesulphonic acidHCID 688558801-(4-Trifluoromethylphenyl)-2-(dimethylhydroxymethyl)-4-hydroxy-6,7-dimethoxynaphthaleneHCID 866199603,4-Dimethoxyphenyl-2-(dimethylhydroxymethyl)-4-hydroxy-6-trifluoromethylnaphthalene

Product 1

HCID 671721412,3-dimethoxy-7,7-dimethyl-9-trifluoromethyl-7H-benzo[C]fluoren-5-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The products from Step 4 (1-(4-trifluoromethylphenyl)-2-(dimethylhydroxymethyl)-4-hydroxy-6,7-dimethoxynaphthalene and 1-(3,4-dimethoxyphenyl-2-(dimethylhydroxymethyl)-4-hydroxy-6-trifluoromethylnaphthalene, 51.7 grams) were placed in a reaction flask equipped with a Dean-Stark trap and 775 mL of toluene was added. The reaction mixture was stirred under a nitrogen atmosphere and dodecylbenzene sulfonic acid (8.3 grams) was added. The reaction mixture was heated to reflux for 5 hours. Upon cooling to room temperature the reaction mixture was concentrated by rotary evaporation. The resulting brown solid was slurried in 300 mL of 15% ethyl acetate/85% hexanes. The solid was collected by vacuum filtration yielding 35.1 grams of 2,3-dimethoxy-7,7-dimethyl-9-trifluoromethyl-7H-benzo[C]fluoren-5-ol. This material was not purified further but was used directly in the next step.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 5 hours
  4. concentrationwas concentrated by rotary evaporation
  5. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-d1c4b3dd9dc94c4ab28ce429096708c3
Source dataset
uspto-grants-2014_06
Patent number
US08748634B2

Linked notes

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