Butyryl chloride → 3-Hydroxy-4-(4-methoxyphenyl)-2-(1-oxobutyl)-2-cyclohexen-1-one

HRID 1649627Notes

Reaction equation

HRID 1649627 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][C:10]2=[O:16])=[CH:5][CH:4]=1.[CH3:17][CH2:18][CH2:19][C:20](Cl)=[O:21].COC1C=CC(C2CCC(OC(=O)CCC)=CC2=O)=CC=1.COC1C=CC(C2C(OC(=O)CCC)=CC(=O)CC2)=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:20]([C:11]1[C:12](=[O:15])[CH2:13][CH2:14][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:10]=1[OH:16])(=[O:21])[CH2:19][CH2:18][CH3:17]

Participants

9

Reactant 4

HCID 8855Butyryl chlorideHCID 19854194HCID 19854194, compoundHCID 19854197HCID 19854197, compoundHCID 19854200HCID 19854200, compound

Product 1

HCID 198541893-Hydroxy-4-(4-methoxyphenyl)-2-(1-oxobutyl)-2-cyclohexen-1-oneYield 86.8%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (11.1 g) was added dropwise to a stirred solution of 4-(4-methoxyphenyl)cyclohexane-1,3-dione (21.8 g) and n-butyryl chloride (17.6 g) in methylene chloride (100 ml) at ambient temperature. After stirring for a further 1 hour, the reaction solution was washed with water, brine and dried over anhydrous magnesium sulphate. The methylene chloride was removed in vacuo to give a mixture of 4-(4-methoxyphenyl)-1-butyryloxycyclohex-1-en-3-one and 6-(4-methoxyphenyl)-1-butyryloxycyclohex-1-ene-3-one. Toluene (150 ml) was added followed by 4-(N,N-dimethylamino) pyridine (0.5 g) and the mixture refluxed for 8 hours. Evaporation of the toluene in vacuo gave a red oil. Purification on a silica gel column using 5% v/v diethyl ether-methylene chloride as eluant gave the title compound (25 g) as an orange oil.

Workup

  1. washthe reaction solution was washed with water, brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customThe methylene chloride was removed in vacuo
  4. customto give
  5. temperaturethe mixture refluxed for 8 hours
  6. customEvaporation of the toluene in vacuo
  7. customgave a red oil
  8. customPurification on a silica gel column

Sources & evidence

ORD record
ord-4bc5b02d2c1640feb961c898dc647735
Source dataset
uspto-grants-1990_05
Patent number
US04921524

Reaction notes

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