Water → HCID 10548453, compound

HRID 2379531Notes

Reaction equation

HRID 2379531 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-1f3fead4f16842528734752e1e2b8122
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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