Hydrochloric Acid → 4-[2-Acetoxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone

HRID 894907Notes

Reaction equation

HRID 894907 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[CH2:17][CH2:18][C:19](=[O:21])[CH3:20].[C:22](OC(=O)C)(=[O:24])[CH3:23].Cl>N1C=CC=CC=1>[C:22]([O:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:15])([CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[CH2:17][CH2:18][C:19](=[O:21])[CH3:20])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 128821664-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone

Product 1

HCID 205749094-[2-Acetoxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2.0 g. of 4-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone in 15 ml. of pyridine is treated at 10° C. with 10 ml. acetic anhydride and the mixture stirred for 18 hours under nitrogen. It is then poured onto ice/water and acidified with dilute hydrochloric acid. The acidified mixture is extracted with ethyl acetate (2×100 ml.), the extracts combined, washed with brine and dried (MgSO4). Evaporation under reduced pressure affords the title product as an oil.

Workup

  1. additionIt is then poured onto ice/water
  2. extractionThe acidified mixture is extracted with ethyl acetate (2×100 ml.)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-3222f760b58342fd91336eb6e09292c4
Source dataset
uspto-grants-1981_08
Patent number
US04284829

Reaction notes

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