Aluminum(III) Chloride → (S)-3-carboxymethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

HRID 35747Notes

Reaction equation

HRID 35747 reaction equation
[CH3:1][C:2]1([CH3:19])[O:6][C:5](=[O:7])[CH2:4][C@@H:3]1[CH2:8][C:9]([CH3:18])([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[C:5]([CH2:4][C@H:3]1[C:2]([CH3:19])([CH3:1])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=2)[C:9]([CH3:18])([CH3:10])[CH2:8]1)([OH:6])=[O:7]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 53670613HCID 53670613, compound

Product 1

HCID 13175027(S)-3-carboxymethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthaleneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (S)-5,5-dimethyl-4-(2-methyl-2-p-tolylpropyl)-tetrahydro-2-furanone (100 mg) in toluene (10 ml), anhydrous aluminum chloride (130 mg) was added, and the resultant mixture was stirred at 70° C. for 30 minutes. The reaction mixture was washed with dilute hydrochloric acid, dried and concentrated to give (S)-3-carboxymethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (95 mg).

Workup

  1. washThe reaction mixture was washed with dilute hydrochloric acid
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4b2ccff2c24145429d9cd724440cd220
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Reaction notes

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