Acetic Acid → HCID 14726496, compound

HRID 1728468Notes

Reaction equation

HRID 1728468 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]1[C:16]2[C:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][C:12]([CH3:20])([CH3:19])[C:11]=2[CH:10]=[C:9]([C:21](Cl)=[O:22])[CH:8]=1.Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1>C(COC)OC.[Zn].C([O-])(=O)C.[Cu+2].C([O-])(=O)C.[Zn].[Cu].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:30]([C:29]1[CH:34]=[CH:35][C:26]([CH2:25][C:21]([C:9]2[CH:8]=[C:7]([O:6][CH3:5])[C:16]3[C:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][C:12]([CH3:20])([CH3:19])[C:11]=3[CH:10]=2)=[O:22])=[CH:27][CH:28]=1)([O:32][CH3:33])=[O:31]

Participants

9

Reactant 3

HCID 176Acetic AcidHCID 256687Methyl 4-(bromomethyl)benzoateHCID 19774811HCID 19774811, compound

Product 1

HCID 14726496HCID 14726496, compoundYield 31.7%

Reagents, catalysts & solvents 5

HCID 8895Cupric acetateCatalystHCID 23994ZincCatalystHCID 10290809Zinc copper coupleCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

2.1 g of zinc powder and 0.21 g of copper(II) acetate were stirred with 7.3 ml of acetic acid at 20° C., with cooling, for 30 min. The zinc/copper couple was filtered off with suction and washed 2x with dry ether and 1x with dry dimethoxyethane. A solution of 4.5 g (16 mmol) of 5,6,7,8-tetrahydro-4-methoxy-5,5,8, 8-tetramethylnaphthalene-2-carbonyl chloride and 3.7 g (16 mmol) of methyl 4-bromomethylbenzoate in 60 ml of dimethoxyethane was added dropwise to a suspension of the zinc/copper couple prepared in this way and of 0.56 g of bis(triphenylphosphine)palladium(II) chloride in 15 ml of dimethoxyethane at room temperature. The mixture was stirred for 75 min and then filtered through Celite, and the filtrate was concentrated. Three recrystallizations of the residue from methanol yielded 2.0 g of the title compound of melting point 143°-144° C.

Workup

  1. temperaturewith cooling, for 30 min
  2. filtrationThe zinc/copper couple was filtered off with suction
  3. washwashed 2x with dry ether and 1x with dry dimethoxyethane
  4. filtrationfiltered through Celite
  5. concentrationthe filtrate was concentrated
  6. customThree recrystallizations of the residue from methanol

Sources & evidence

ORD record
ord-fd634e56a63b4dd887b9a612f9528ee9
Source dataset
uspto-grants-1994_07
Patent number
US05326900

Reaction notes

Loading…