Potassium Carbonate → Dimethyl 4-[3-[4-(3,3-dimethyl-2-oxobutoxy)-3-ethylphenyl]propyl}phthalate

HRID 970835Notes

Reaction equation

HRID 970835 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([C:23]([O:25][CH3:26])=[O:24])[C:16](=[CH:21][CH:22]=2)[C:17]([O:19][CH3:20])=[O:18])[CH:6]=[CH:7][C:8]=1[OH:9])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>CC(=O)CC>[CH3:37][C:36]([CH3:39])([CH3:38])[C:35](=[O:40])[CH2:34][O:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[C:15]([C:23]([O:25][CH3:26])=[O:24])[C:16](=[CH:21][CH:22]=2)[C:17]([O:19][CH3:20])=[O:18])=[CH:4][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 17983037Dimethyl 4-[3-(3-ethyl-4-hydroxyphenyl)propyl]phthalate

Product 1

HCID 17982979Dimethyl 4-[3-[4-(3,3-dimethyl-2-oxobutoxy)-3-ethylphenyl]propyl}phthalate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

800 mg (2.2 mmol) of dimethyl 4-[3-(3-ethyl-4-hydroxyphenyl)propyl}phthalate are dissolved in 40 ml of 2-butanone. 340 mg (2.5 mmol) of potassium carbonate and 330 μl (2.5 mmol) of 1-bromopinacolone are added. The reaction medium is heated under reflux for 8 hours, and is then filtered on celite. The residue obtained is purified by chromatography on a silica column (eluent ethyl acetate 20/heptane 80). A colorless oil is obtained (m=920 mg; y=90%).

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureunder reflux for 8 hours
  3. filtrationis then filtered on celite
  4. customThe residue obtained
  5. customis purified by chromatography on a silica column (eluent ethyl acetate 20/heptane 80)
  6. customA colorless oil is obtained (m=920 mg; y=90%)

Sources & evidence

ORD record
ord-110d3e55b0f545528d7e05dde786c3f6
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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