Acetic Anhydride → HCID 58972222, compound

HRID 922074Notes

Reaction equation

HRID 922074 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14]/[CH:15]=[C:16](\[CH3:22])/[CH2:17][CH2:18][CH2:19][CH2:20][OH:21].[CH3:23][C:24](OC(C)=O)=[O:25]>N1C=CC=CC=1>[C:24]([O:21][CH2:20][CH2:19][CH2:18][CH2:17]/[C:16](/[CH3:22])=[CH:15]/[CH2:14][C:4]1[C:5]([CH3:13])=[C:6]([O:11][CH3:12])[C:7]([CH3:10])=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1])(=[O:25])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58972225HCID 58972225, compound

Product 1

HCID 58972222HCID 58972222, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-en-1-ol in pyridine (2 mL) was treated with Ac2O (2 mL) at 0° C. and let stir overnight. The reaction was quenched with H2O (10 mL) followed by addition of EtOAc (10 mL) and separated. The aqueous phase was extracted with EtOAc (3×10 mL) and the combined organics washed with brine (15 mL), dried over anhydrous Na2SO4 and concentrated to a yellow oil. Flash chromatography on silica yielded 77.9 mg (62.3%) of (E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-enyl acetate as a clear oil.

Workup

  1. customThe reaction was quenched with H2O (10 mL)
  2. additionfollowed by addition of EtOAc (10 mL)
  3. customseparated
  4. extractionThe aqueous phase was extracted with EtOAc (3×10 mL)
  5. washthe combined organics washed with brine (15 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-f9aa7b06bc6541eb9c0d2354c7c50645
Source dataset
uspto-grants-2016_03
Patent number
US09278085B2

Reaction notes

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