Hydrochloric Acid → (S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthalene

HRID 35749

Reaction equation

HRID 35749 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl[CH2:8][C@@H:9]1[C:18]([CH3:20])([CH3:19])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:21])[CH:16]=2)[C:11]([CH3:23])([CH3:22])[CH2:10]1.Cl>O1CCCC1>[CH3:22][C:11]1([CH3:23])[C:12]2[C:17](=[CH:16][C:15]([CH3:21])=[CH:14][CH:13]=2)[C:18]([CH3:20])([CH3:19])[C@@H:9]([CH3:8])[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13175029(S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthaleneHCID 21226445Aluminium lithium hydride

Product 1

HCID 13175223(S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthaleneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium aluminum hydride (9.56 g; 0.252 mol) in tetrahydrofuran (70 ml) under a nitrogen stream, a solution of (S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 26.1° (C=1 in n-hexane)) (62.9 g; 0.251 mol) in tetrahydrofuran was dropwise added. After refluxing for 15 hours, the reaction mixture was treated with aqueous tetrahydrofuran in nitrogen, admixed with 5% hydrochloric acid (600 ml) and extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried, concentrated and distilled to give (S)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (46.0 g; 0.213 mol; 85%). [α]546 -49.1° (C=1 in chloroform). B.P., 91° C./0.5 mmHg.

Workup

  1. temperatureAfter refluxing for 15 hours
  2. extractionextracted with n-hexane
  3. washThe extract was washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-e9cda3ec3f69499e905ef4fbde7d66e4
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Linked notes

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