Sodium Hydroxide → HCID 22799128, compound

HRID 867142Notes

Reaction equation

HRID 867142 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][C@H:6]([CH3:18])[CH2:7][CH2:8][CH2:9][C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])C.[OH-].[Na+]>CO>[CH3:18][C@H:6]([CH2:7][CH2:8][CH2:9][C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:5][C:4]([OH:19])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14267002HCID 14267002, compound

Product 1

HCID 22799128HCID 22799128, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

145 mg of 3(R),7(R),11-trimethyl-dodecanoic acid ethyl ester and 0.5 ml of 6 N aqueous NaOH were refluxed in 3 ml of methanol for 2.0 hr. The methanol was removed at reduced pressure and water (100 ml) was added. The aqueous alkaline solution was extracted with diethyl ether (2 × 30 ml), cooled in an ice-bath, and acidified with concentrated hydrochloric acid. The acidic aqueous solution was extracted with diethyl ether (3 × 20 ml). The combined ether extract was washed with water (3 × 20 ml) and dried (MgSO4). Evaporation of ether to dryness at reduced pressure gave 107 mg of light yellow oil, which was distilled (Kugelrohr 135°-139°/0.2 mm) to yield 101 mg of 3(R),7,(R),11-trimethyl-dodecanoic acid as a colorless oil.

Workup

  1. customThe methanol was removed at reduced pressure and water (100 ml)
  2. additionwas added
  3. extractionThe aqueous alkaline solution was extracted with diethyl ether (2 × 30 ml)
  4. temperaturecooled in an ice-bath
  5. extractionThe acidic aqueous solution was extracted with diethyl ether (3 × 20 ml)
  6. extractionThe combined ether extract
  7. washwas washed with water (3 × 20 ml)
  8. dry with materialdried (MgSO4)
  9. customEvaporation of ether to dryness at reduced pressure

Sources & evidence

ORD record
ord-90bc9b270cf046ff9bcea062478c3d35
Source dataset
uspto-grants-1978_07
Patent number
US04102909

Reaction notes

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