Iodine → 4,4-Dimethylpentanoic acid

HRID 1737157Notes

Reaction equation

HRID 1737157 reaction equation
Cl[CH2:2][CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[Mg].II.[OH-:11].[Na+].C([O:15][CH2:16]C)C>>[CH3:5][C:4]([CH3:7])([CH3:6])[CH2:3][CH2:2][C:16]([OH:15])=[O:11]

Participants

6

Reactant 5

HCID 807IodineHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 761111-Chloro-3,3-dimethylbutaneHCID 5462224Magnesium

Product 1

HCID 142374,4-Dimethylpentanoic acid

Procedure

1-Chloro-3,3-dimethylbutane (log) was added dropwise to magnesium turnings (2 g) with an initiating amount of iodine crystals in dry diethyl ether (100 ml) and Grignard formation allowed to proceed to completion over 1 hour. The mixture was poured onto dry ice (50 g) very slowly and 0.5 N sodium hydroxide added and the basic aqueous layer provided extracted with diethyl ether (x2). The basic aqueous layer was acidified and extracted with diethyl ether which was dried over magnesium sulphate, filtered then evaporated under vacuum to yield 7.2 g of 4,4-dimethyl pentanoic acid.

Workup

  1. additionThe mixture was poured onto dry ice (50 g) very slowly
  2. customthe basic aqueous layer provided
  3. extractionextracted with diethyl ether (x2)
  4. extractionextracted with diethyl ether which
  5. dry with materialwas dried over magnesium sulphate
  6. filtrationfiltered
  7. customthen evaporated under vacuum

Sources & evidence

ORD record
ord-8175fc262f164bbb8d20ad56d81cc2aa
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

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