Lithium Chloride → 2-Chloromethyl-1,1,4,4,6-pentamethyl1,2,3,4-tetrahydronaphthalene

HRID 35752Notes

Reaction equation

HRID 35752 reaction equation
C([CH2:4][CH:5]1[CH2:14][C:13]([CH3:16])([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:17])[CH:11]=2)[C:6]1([CH3:19])[CH3:18])(O)=O.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].[Cl-:37].[Li+]>C1C=CC=CC=1>[Cl:37][CH2:4][CH:5]1[CH2:14][C:13]([CH3:16])([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:17])[CH:11]=2)[C:6]1([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 143438932-Carboxymethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 178418268HCID 178418268, compound

Product 1

HCID 143438962-Chloromethyl-1,1,4,4,6-pentamethyl1,2,3,4-tetrahydronaphthaleneYield 65.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-carboxymethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (30 g; 0.115 mol) in benzene (570 g), lead tetraacetate (66 g; 0.149 mol) and anhydrous lithium chloride (11.5 g; 0.271 mol) were added, and the temperature was elevated up to 80° C. After stirring for 6.5 hours, the reaction mixture was washed with water and dilute hydrochloric acid in order. After extraction of the unreacted carboxylic acid with 6% ammonia water, the benzene layer was dried over anhydrous sodium sulfate and concentrated to give 2-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (18.9 g; 0.075 mol). From the ammonia water layer, there was recovered the unreacted carboxylic acid (9.8 g).

Workup

  1. customwas elevated up to 80° C
  2. washthe reaction mixture was washed with water and dilute hydrochloric acid in order
  3. extractionAfter extraction of the unreacted carboxylic acid with 6% ammonia water
  4. dry with materialthe benzene layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e58c3ee12e4d426cae2ec035c5c58c1e
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Reaction notes

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