Hydrochloric Acid → 12-Benzyloxy-2,2-dimethyldodecanoic acid

HRID 371266Notes

Reaction equation

HRID 371266 reaction equation
[Li].[CH3:2][CH:3]([CH3:7])[C:4]([OH:6])=[O:5].C([N-]C(C)C)(C)C.[Li+].[CH2:16]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O1CCCC1>[CH2:16]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:3]([CH3:7])([CH3:2])[C:4]([OH:6])=[O:5])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6590Isobutyric AcidHCID 2724682Lithium diisopropylamideHCID 3028194LithiumHCID 13478286(((10-Bromodecyl)oxy)methyl)benzene

Product 1

HCID 1347828912-Benzyloxy-2,2-dimethyldodecanoic acidYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the method reported by George R. Newkome et al.: Synthesis, 1975, 517, lithium dianion of 2-methylpropionic acid was generated from lithium diisopropylamide in tetrahydrofuran under a nitrogen atmosphere. After the dropwise addition thereto of 18 g of 10-benzyloxydecanyl bromide at -20° C., the mixture was reacted at 45° C. for 2 hours. The reaction mixture was then mixed with cold dilute hydrochloric acid and extracted with ether, and the separated ether layer was washed with dilute hydrochloric acid and then with water. The separated layer was then dried over salt cake and evaporated to dryness to leave a crude oily material which in turn was recrystallized from petroleum ether, producing 8.4 g (yield 46%) of 12-benzyloxy-2,2-dimethyldodecanoic acid as colorless crystal. M.P. 53° to 55° C.

Workup

  1. additionAfter the dropwise addition
  2. extractionextracted with ether
  3. washthe separated ether layer was washed with dilute hydrochloric acid
  4. dry with materialThe separated layer was then dried over salt cake
  5. customevaporated to dryness
  6. customto leave a crude oily material which in turn
  7. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-03116a0512c541ef95d5bb46badd03a7
Source dataset
uspto-grants-1985_07
Patent number
US04530794

Reaction notes

Loading…