Methane, dichloromethoxy- → HCID 11593950, compound

HRID 1756993Notes

Reaction equation

HRID 1756993 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5]([CH3:15])([CH3:14])[CH2:4][CH2:3]1.[CH:17]([O:20]C)(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:13][C:7]1[C:6]2[C:5]([CH3:15])([CH3:14])[CH2:4][CH2:3][C:2]([CH3:16])([CH3:1])[C:11]=2[CH:10]=[C:9]([CH3:12])[C:8]=1[CH:17]=[O:20]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 138132891,1,4,4,5,7-Hexamethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 11593950HCID 11593950, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1,2,3,4-tetrahydro-1,1,4,4,5,7-hexamethylnaphthalene (5.0 g) of TiCl4 (7.32 g) in methylene chloride (40 ml) was treated with Cl2CHOCH3 (2.66 g) in methylene chloride (5 ml), at 0° and over 20 min. The temperature of the reaction mixture was allowed to reach 20° (20 min) and said mixture was then poured on ice water and extracted with ether. The organic phase was successively washed with a 10% aqueous solution of NaOH, water and an aqueous solution saturated with NaCl, then dried over Na2SO4, evaporated and recrystallized from methanol. 4.06 g (yield 72%) of 5,6,7,8-tetrahydro-1,3,5,5,8,8-hexamethyl-2-naphthalenecarbaldehyde were obtained, the product being identical in data to that described in b).

Workup

  1. customto reach 20°
  2. custom(20 min)
  3. additionwas then poured on ice water
  4. extractionextracted with ether
  5. washThe organic phase was successively washed with a 10% aqueous solution of NaOH, water
  6. dry with materialan aqueous solution saturated with NaCl, then dried over Na2SO4
  7. customevaporated
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8a1ef52a4e414896bf13b578b062712b
Source dataset
uspto-grants-1995_08
Patent number
US05442124

Reaction notes

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