Hydrochloric Acid → HCID 14343905, compound

HRID 35756Notes

Reaction equation

HRID 35756 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].Cl[CH2:8][CH2:9][C@H:10]1[C:19]([CH3:21])([CH3:20])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:22])[CH:17]=2)[C:12]([CH3:24])([CH3:23])[CH2:11]1.Cl>O1CCCC1>[CH2:9]([C@H:10]1[C:19]([CH3:21])([CH3:20])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:22])[CH:17]=2)[C:12]([CH3:23])([CH3:24])[CH2:11]1)[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14343902HCID 14343902, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14343905HCID 14343905, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of aluminum lithium hydride (6.5 g; 0.171 mol) in tetrahydrofuran (100 ml), a solution of (S)-3-(2-chloroethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 --33.4° (C=1.17 in ethanol)) (44.8 g; 0.169 mol) in tetrahydrofuran was dropwise added thereto. The resultant mixture was heated with reflux for 12 hours and then cooled. The cooled mixture was treated with dilute hydrochloric acid and extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give (R)-3-ethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (37.0 g; 0.161 mol; 94%). B.P., 79°-80° C./0.15 mmHg. [α]546 +2.2° (C=0.95 in ethanol).

Workup

  1. temperaturewith reflux for 12 hours
  2. temperaturecooled
  3. extractionextracted with n-hexane
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-188bc9bc7f564649b830b4a164b7c109
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Reaction notes

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