Water → HCID 20469262, compound

HRID 1388632Notes

Reaction equation

HRID 1388632 reaction equation
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][C:5]1(C(OC)=O)[CH:10]([CH3:11])[CH2:9][C:8]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:7][C:6]1=[O:16].[Cl-].[Li+].O>CN(C)P(=O)(N(C)C)N(C)C>[CH:13]([O:12][C:8]1[CH2:9][CH:10]([CH3:11])[CH:5]([CH2:4][CH:3]=[C:2]([CH3:21])[CH3:1])[C:6](=[O:16])[CH:7]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 20469326HCID 20469326, compound

Product 1

HCID 20469262HCID 20469262, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
130 °C

Procedure

Reaction: ##STR31## To a solution of methyl 1-(3-methyl-2-butenyl)-2-oxo-4-isopropoxy-6-methyl-3-cyclohexene carboxylate (29.4 g, 0.1 mol) in anhydrous hexamethylphosphoric triamide (220 mL) was added anhydrous lithium chloride (6.4 g, 0.15 mol). The mixture was stirred at 130° C. in a nitrogen atmosphere for 1.5 hours and then added to water (800 mL). The aqueous solution was extracted with ether. The combined ether extracts were washed with water and dried (Na2SO4). The ether was removed on a rotary evaporator and the residue vacuum distilled, yielding 20.1 g of 3-isopropoxy-5-methyl-6-(3-methyl-2-butenyl)-2-cyclohexen-1-one, bp 104°-108° C./0.05 mm. The product was shown by glc/ms to be a mixture of "cis" and "trans" isomers in a ratio of 76:24.

Workup

  1. customReaction
  2. extractionThe aqueous solution was extracted with ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customThe ether was removed on a rotary evaporator
  6. distillationthe residue vacuum distilled

Sources & evidence

ORD record
ord-70f743f23481486dba07e70ae989a55b
Source dataset
uspto-grants-1984_02
Patent number
US04432378

Reaction notes

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