Benzoyl chloride → HCID 67201259, compound

HRID 544813Notes

Reaction equation

HRID 544813 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH:11]1[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][CH:12]1[C:19](=[O:24])[CH2:20][CH2:21][CH:22]=[CH2:23].CCN(CC)CC.CCOC(C)=O.C1CCCCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:10][C@@H:11]1[CH2:16][CH2:15][C:14]([CH3:17])([CH3:18])[CH2:13][C@@H:12]1[C:19](=[O:24])[CH2:20][CH2:21][CH:22]=[CH2:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 21867204Cyclohexane ethylacetateHCID 672014931-(2-Hydroxy-5,5-dimethylcyclohexyl)pent-4-en-1-one

Product 1

HCID 67201259HCID 67201259, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

Benzoyl chloride (12.8 g, 91 mmoles) was added dropwise to a stirred solution of 1-(2-hydroxy-5,5-dimethyl-1-cyclohexyl)-4-penten-1-one (16 g, 75 mmoles), Et3N (10 g, 99 mmoles) and DMAP (1.8 g, 15 mmoles) in CH2Cl2 (380 ml) at 20° C. and under nitrogen. The solution was heated at 45° C. during 22 hours, cooled to room temperature and washed successively with 5% aqueous HCl, 10% aqueous Na2CO3, and again with water. The organic phase was dried over Na2SO4 and concentrated to afford a brown oil. Chromatography (SiO2, AcOEt/Cyclohexane 1:9) and afforded 6.7 g of the title compound (yield=28%).

Workup

  1. temperaturecooled to room temperature
  2. washwashed successively with 5% aqueous HCl, 10% aqueous Na2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customto afford a brown oil

Sources & evidence

ORD record
ord-b23b071b319f4df2a067183d468ea3a9
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

Loading…