Hydrochloric Acid → HCID 14343908, compound

HRID 35759Notes

Reaction equation

HRID 35759 reaction equation
[CH2:1]([C@H:3]1[C:12]([CH3:14])([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:15])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[CH2:4]1)[CH3:2].[C:18](Cl)(=[O:20])[CH3:19].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[C:18]([C:8]1[CH:7]=[C:6]2[C:11]([C:12]([CH3:14])([CH3:13])[C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]2([CH3:16])[CH3:17])=[CH:10][C:9]=1[CH3:15])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14343905HCID 14343905, compound

Product 1

HCID 14343908HCID 14343908, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (R)-3-ethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 +2.2° (C=0.95 in ethanol)) (36.5 g; 0.159 mol) and acetyl chloride (13.7 g; 0.174 mol) in 1,2-dichloroethane (100 ml), anhydrous aluminum chloride (25.3 g; 0.190 mol) was added at 20° C., and the resulting mixture was stirred for 1 hour. The reaction mixture was treated with dilute hydrochloric acid while cooling with ice. The organic layer was washed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order, dried over anhydrous sodium sulfate and concentrated t give (R)-7-acetyl-3-ethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (41.5 g; 0.153 mol; 96%). B.P., 120° C./0.1 mmHg. [α]365 -46.1° (C=0.97 in ethanol).

Workup

  1. temperaturewhile cooling with ice
  2. washThe organic layer was washed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4611be62778c4d61964b2be22c1c880d
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Reaction notes

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