Hydrochloric Acid → HCID 178467885, compound

HRID 1653836Notes

Reaction equation

HRID 1653836 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Li+].[CH3:17][Li].Cl>COCCOC.CCOCC.O>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH2:11][C:12](=[O:14])[CH3:17])[CH2:9][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 62714Lithium hydrideHCID 178418348HCID 178418348, compoundHCID 178445625HCID 178445625, compound

Product 1

HCID 178467885HCID 178467885, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of trans-(4-t-butylcyclohexyl)acetic acid (9.96 g) in dry DME (30 ml) was added over 10 min to a vigorously stirred suspension of powdered lithium hydride (0.5 g) in dry DME (30 ml). The mixture was refluxed for 2.5 hr, cooled on ice and a solution of methyl lithium in ether (63 ml; 1.6M solution) added over 30 min. The mixture was then stirred at room temperature for 2 hr, and poured into a mixture of conc. hydrochloric acid (13.5 ml) and water (200 ml). The organic phase was separated and the residue extracted with ether. The extracts were combined, washed with aq. sodium carbonate and satd. brine, dried over magnesium sulphate and concentrated in vacuo. Distillation afforded the title compound (7.7 g), b.p. 90°-100°/0.3 mm, NMR δH (CDCl3) 2.28 (2H, d, J 7Hz), 2.12 (3H, s), 1.85-1.65 (6H, m), 1.05-0.85 (4H, m), 0.85 (9H, s).

Workup

  1. temperatureThe mixture was refluxed for 2.5 hr
  2. temperaturecooled on ice
  3. customThe organic phase was separated
  4. extractionthe residue extracted with ether
  5. washwashed with aq. sodium carbonate
  6. dry with materialbrine, dried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. distillationDistillation

Sources & evidence

ORD record
ord-2ec0e05828c741908560d5a10fd38986
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

Loading…