Hydrochloric Acid → Ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate

HRID 1823649Notes

Reaction equation

HRID 1823649 reaction equation
[Mg].[C:2]1([CH2:8][CH2:9][C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl[Si](C)(C)C.Cl>C1COCC1>[OH:14][C:10]([CH2:9][CH2:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH2:11][CH2:12][CH3:13])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7751Ethyl chloroacetateHCID 1225021-Phenylhexan-3-oneHCID 5462224Magnesium

Product 1

HCID 10149285Ethyl 3-hydroxy-3-(2-phenylethyl)hexanoateYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium (13.6 g, 0.559 mole) was suspended in THF (50 mL), and thereto was added a mixture of 1-phenyl-3-hexanone (20.09 g, 0.114 mole), ethyl chloroacetate (34.8 g, 0.284 mole) and chlorotrimethylsilane (15.4 g, 0.142 mole) at 20° C.-30° C. over 180 min in a thin stream. The mixture was stirred at 20° C.-30° C. for 2 hr and treated with diluted hydrochloric acid to give a THF solution containing ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate (21.8 g, yield: 72.3%; quantified by absolute calibration curve method (external standard method) using HPLC).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-bba32f6a9b424373a3d0c1031ac25aa4
Source dataset
uspto-grants-2006_05
Patent number
US07038075B2

Reaction notes

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