Water → HCID 10548453, compound

HRID 488158Notes

Reaction equation

HRID 488158 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12]/[C:13](/[CH2:18][CH2:19]/[CH:20]=[C:21](\[CH3:28])/[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:14]\[CH2:15][CH2:16][OH:17].O>N1C=CC=CC=1>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O:17][CH2:16][CH2:15]/[CH:14]=[C:13](\[CH3:12])/[CH2:18][CH2:19]/[CH:20]=[C:21](\[CH3:28])/[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 10243212Homofarnesol

Product 1

HCID 10548453HCID 10548453, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Tosylchloride (3.51 g, 9 mmol) was added to a stirred solution of (E,E)-4,8,12-trimethyl-3,7,11-tridecatrienol (1.66 g, 7 mmol) in pyridine (30 mL) at 0° C. The resulting mixture was placed in a refrigerator overnight, then poured into cold water and extracted with ether. The ethereal extract was washed with diluted hydrochloric acid to remove pyridine. After drying and filtration, the filtrate was evaporated to afford the title compound as an oil which was used in the next step without purification.

Workup

  1. customwas placed in a refrigerator overnight
  2. extractionextracted with ether
  3. extractionThe ethereal extract
  4. washwas washed with diluted hydrochloric acid
  5. customto remove pyridine
  6. customAfter drying
  7. filtrationfiltration
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d00757c3e851439db5c3a3df780f67f2
Source dataset
uspto-grants-1994_03
Patent number
US05298655

Reaction notes

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