Sodium Hydroxide → HCID 89650178, compound

HRID 2275990Notes

Reaction equation

HRID 2275990 reaction equation
[CH2:1]([C:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[C:5]=1[CH2:12][C:13]([O:15]CC1C=CC=CC=1)=[O:14])[CH:2]=[CH2:3].[OH-].[Na+]>O1CCOCC1.O>[CH2:1]([C:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[C:5]=1[CH2:12][C:13]([OH:15])=[O:14])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89650431HCID 89650431, compound

Product 1

HCID 89650178HCID 89650178, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of benzyl 2-(2-allyl-6,6-dimethyl-cyclohexen-1-yl)acetate (1.5 g, 5.02 mmol) in dioxane (12 mL) and water (4 mL) was added NaOH (2M, 5.5 mL). The solution was heated to 100° C. for 30 h. The solution was concentrated in vacuo and water was added. The aqueous layer was extracted 2 times with ether and the organic layer was removed. Then, pH of the aqueous layer was adjusted to 1. The solution was extracted with ethyl acetate and washed with brine, dried and concentrated to give the desired product as a colourless oil (1.05 g, quant). 1H NMR (400 MHz, CDCl3) δ 5.77 (1H, dd, J=16.9, 10.3 Hz), 4.88-5.09 (2H, m), 3.13 (2H, s), 2.74 (2H, d, J=6.2 Hz), 1.96-2.08 (2H, m), 1.59-1.69, (2H, m), 1.43-1.57 (2H, m), 0.98-1.06 (6H, s) ppm.

Workup

  1. concentrationThe solution was concentrated in vacuo and water
  2. additionwas added
  3. extractionThe aqueous layer was extracted 2 times with ether
  4. customthe organic layer was removed
  5. extractionThe solution was extracted with ethyl acetate
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-97ed35c62c3d453ba2eadf24556b2c0e
Source dataset
uspto-grants-2015_09
Patent number
US09131688B2

Reaction notes

Loading…