Water → HCID 54242128, compound

HRID 364648Notes

Reaction equation

HRID 364648 reaction equation
[Br-].[CH3:2][C:3]1[CH2:8][CH2:7][CH2:6][C:5]([CH3:10])([CH3:9])[C:4]=1[CH:11]=[CH:12][CH:13]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:14].[H-].[Na+].[CH3:36][C:37]1[C:44]([CH3:45])=[C:43]([O:46][CH3:47])[CH:42]=[C:41]([CH3:48])[C:38]=1[CH:39]=O.O>CN(C)C=O>[CH3:47][O:46][C:43]1[CH:42]=[C:41]([CH3:48])[C:38]([CH:39]=[C:13]([CH3:14])[CH:12]=[CH:11][C:4]2[C:5]([CH3:9])([CH3:10])[CH2:6][CH2:7][CH2:8][C:3]=2[CH3:2])=[C:37]([CH3:36])[C:44]=1[CH3:45]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8241424-Methoxy-2,3,6-trimethylbenzaldehydeHCID 73666441HCID 73666441, compound

Product 1

HCID 54242128HCID 54242128, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-yl]triphenylphosphonium bromide (prepared from 17.2 g of 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-ol and 30.4 g of triphenylphosphonium hydrogen bromide in 150 mL of N,N-dimethylformamide (DMF)) was stirred under nitrogen in an ice bath and NaH (4.25 g, 50% oil dispersion) was added in portions. The mixture was stirred in the cooling bath for an additional hour and a solution of 2,3,6-trimethyl-p-anisaldehyde (15.8 g, 0.089 mol) in 50 mL of DMF was added dropwise within 15 min. The resulting mixture was stirred at room temperature for 18 hrs and heated to 50°-60° C. for 11/2 hrs. After cooling, the mixture was poored into 3 liters of water and extracted with hexane. The hexane extract was washed with 400 mL of a MeOH:H2O mixture (6:4, v/v) and water (400 mL). After drying over Na2SO4, the solvent was evaporated in vacuo to give 24.1 g of crude product as a brown oil. The pure product was obtained as a pale yellow oil from vacuum distillation of the crude product, bp. 152°-153° C. (0.075 mm of Hg); MS (CI): 339 (m+ +1).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 18 hrs
  2. temperatureheated to 50°-60° C. for 11/2 hrs
  3. temperatureAfter cooling
  4. extractionextracted with hexane
  5. extractionThe hexane extract
  6. washwas washed with 400 mL of a MeOH
  7. dry with materialAfter drying over Na2SO4
  8. customthe solvent was evaporated in vacuo
  9. customto give 24.1 g of crude product as a brown oil

Sources & evidence

ORD record
ord-f6b3efb4abc44280818d151f6699cdee
Source dataset
uspto-grants-1986_08
Patent number
US04605675

Reaction notes

Loading…