(1-Cyanocyclohexyl)acetic acid → HCID 23672403, compound

HRID 654581Notes

Reaction equation

HRID 654581 reaction equation
CC(C)([O-])C.[K+:6].[C:7]([C:9]1([CH2:15][C:16]([OH:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)#[N:8]>O1CCCC1>[C:7]([C:9]1([CH2:15][C:16]([O-:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)#[N:8].[K+:6]

Participants

4

Reactant 2

HCID 11073797(1-Cyanocyclohexyl)acetic acidHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 23672403HCID 23672403, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 250-mL flask under nitrogen is added 14.8 g (0.13 mol) of potassium tertiary butoxide followed by 74 mL of tetrahydrofuran. The solution is stirred for 10 minutes, suction filtered, and washed using 50 mL of tetrahydrofuran. The filtrates are combined and transferred into an addition funnel on a separate 250-mL flask containing 20 g (0.12 mol) of dried 1-cyanocyclohexaneacetic acid and 100 mL of tetrahydrofuran. The potassium tertiary butoxide solution is added dropwise over 5 minutes to the previous solution. The precipitate is cooled in an ice bath, suction filtered, and washed with 25 mL of cold tetrahydrofuran. The filter cake is dried in a vacuum oven at 50° C. for 16 hours to give 24.8 g of potassium 1-cyanocyclohexaneacetate as a white crystalline solid; mp 196-199° C.

Workup

  1. filtrationsuction filtered
  2. washwashed
  3. customtransferred into an addition funnel on a separate 250-mL flask
  4. temperatureThe precipitate is cooled in an ice bath
  5. filtrationsuction filtered
  6. washwashed with 25 mL of cold tetrahydrofuran
  7. customThe filter cake is dried in a vacuum oven at 50° C. for 16 hours

Sources & evidence

ORD record
ord-3f21a2ce0e16475cb6b0a5e26dd28b34
Source dataset
uspto-grants-1992_07
Patent number
US05132451

Reaction notes

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