Aluminum(III) Chloride → HCID 18357927, compound

HRID 428219Notes

Reaction equation

HRID 428219 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[CH:10]=[C:9]([C:12](Cl)=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[OH:16][C:17]1[CH:26]=[C:25]([C:27]#[C:28][Si](C)(C)C)[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[OH:16][C:17]1[CH:26]=[C:25]([C:27]#[C:28][C:12](=[O:13])[C:9]2[CH:8]=[CH:7][C:6]3[CH2:5][CH2:4][CH2:3][C:2]([CH3:15])([CH3:1])[C:11]=3[CH:10]=2)[CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 183579338,8-Dimethyl-5,6,7,8-tetrahydro-2-naphthoyl chlorideHCID 22641103Methyl 2-hydroxy-4-trimethylsilylethynylbenzoate

Product 1

HCID 18357927HCID 18357927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12 g (54 mmol) of 8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthoyl chloride, 14.7 g (59 mmol) of methyl 2-hydroxy-4-trimethylsilylethynylbenzoate (prepared in Example 5(a) of patent EP 0,661,258) and 200 ml of dichloromethane are introduced into a round-bottomed flask. 21.6 g (162 mmol) of AlCl3 are added portionwise at 0° C. and the mixture is stirred at room temperature for 8 hours. The reaction medium is poured into ice and extracted with dichloromethane, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of dichloromethane and hexane (50/50). 12.5 g (64%) of the expected product are collected, with a melting point of 114-6° C.

Workup

  1. additionThe reaction medium is poured into ice
  2. extractionextracted with dichloromethane
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of dichloromethane and hexane (50/50)
  9. custom12.5 g (64%) of the expected product are collected, with a melting point of 114-6° C.

Sources & evidence

ORD record
ord-318025d139164598a4061ffc998cf0b7
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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