Hydrochloric Acid → HCID 14348621, compound

HRID 236249Notes

Reaction equation

HRID 236249 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[C:11]1([CH2:20][C:19](=[O:21])[CH:18]([C:22](=[O:25])[CH2:23][CH3:24])[C:17](=[O:26])[CH2:16]1)[CH2:10][CH2:9]2.[C:27](Cl)(=[O:29])[CH3:28].Cl>ClCCCl.ClC(Cl)C>[C:27]([C:14]1[C:13]([CH3:15])=[C:12]2[C:8]([CH2:9][CH2:10][C:11]32[CH2:16][C:17](=[O:26])[CH:18]([C:22](=[O:25])[CH2:23][CH3:24])[C:19](=[O:21])[CH2:20]3)=[CH:7][C:6]=1[CH3:5])(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14348619HCID 14348619, compound

Product 1

HCID 14348621HCID 14348621, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a stirred suspension of aluminium trichloride (4.8 g, 33 mmol) in 1,2-dichloroethane (80 ml) at 20° C. was added a solution of 5', 7'-dimethyl-4-propionylspiro[cyclohexane-1,1'-indan]-3,5-dione (3.2 g, 11 mmol) in dichloroethane (10 ml). A solution of acetyl chloride (1.0 g, 13 mmol) in dichloroethane (10 ml) was added and the mixture was stirred at 20° C. for 12 hours. The solution was poured onto cold dilute hydrochloric acid and then extracted with diethyl ether. The ether layer was separated, dried (MgSO4) and evaporated and the crude product was purified by passage through silica gel eluting with methylene chloride. A mixture of 4'-acetyl-5',7'-dimethyl-4-propionylspiro[cyclohexane-1,1'-indan]-3,5-dione and 6'-acetyl-5',7'-dimethyl-4-propionylspiro[cyclohexane-1,1'-indan]-3,5-dione was obtained as a colourless oil (1.0 g, 29%). Pmr spectrum (CDCl3, δ in ppm): 1.16 (3H, t); 1.9-3.3 (17H, complex m); 3.09 (2H, q); 6.84 (0.6H, s); 6.93 (0.4H, s); 18.26 (1H, s).

Workup

  1. extractionextracted with diethyl ether
  2. customThe ether layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe crude product was purified by passage through silica gel eluting with methylene chloride
  6. additionA mixture of 4'-acetyl-5',7'-dimethyl-4-propionylspiro[cyclohexane-1,1'-indan]-3,5-dione

Sources & evidence

ORD record
ord-f59cf0d5ecc441939c3b03167020987a
Source dataset
uspto-grants-1987_02
Patent number
US04643763

Reaction notes

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