Ethylparaben → HCID 86584486, compound

HRID 394917Notes

Reaction equation

HRID 394917 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][OH:16])[CH:5]=[CH:4][C:3]1=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:43]1[CH:53]=[CH:52][C:46]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:45][CH:44]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OCC)C>[CH3:1][C:2]1([CH3:22])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][O:16][C:43]3[CH:53]=[CH:52][C:46]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:45][CH:44]=3)[CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 17949402HCID 17949402, compound

Product 1

HCID 86584486HCID 86584486, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

400 mg of (RS)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-heptanol dissolved in 25 ml of THF absolute were treated with 382 mg of triphenylphosphine, 242 mg of ethyl 4-hydroxybenzoate and 0.24 ml of diethyl azodicarboxylate. The reaction mixture was heated to reflux for 6 hours. The mixture was diluted with 1 portion of 50 ml of diethylether and washed with 2 portions of 25 ml of water and 1 portion of 50 ml of a saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated in vacuo. The resulting yellow oil was purified by flash chromatography (SiO2, 3% ethyl acetate/hexanes), giving 591 mg of (RS)-ethyl 4-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-heptyloxy]-benzoate as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. washwashed with 2 portions of 25 ml of water and 1 portion of 50 ml of a saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting yellow oil was purified by flash chromatography (SiO2, 3% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4a7fcdc3f0de4e1f9e1b4af073517a46
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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