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

HRID 1823650Notes

Reaction equation

[Mg].II.[C:4]1([CH2:10][CH2:11][C:12](=[O:16])[CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl>C1COCC1>[OH:16][C:12]([CH2:11][CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH2:13][CH2:14][CH3:15])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

Conditions

Temperature: 30 °C

Procedure

Magnesium (1.98 g, 81.4 mmole) was suspended in THF (15 mL), and iodine (10 mg) was added thereto. To the suspension was added 1 mL from a mixture (total amount: 20 mL) of 1-phenyl-3-hexanone (8.93 g, 50.7 mmole) and ethyl chloroacetate (9.94 g, 81.1 mmole) at 25° C. in a thin stream. The mixture was stirred for 10 min and allowed to warm the internal temperature to 30° C. The remaining (19 mL) of the above-mentioned mixture (total amount: 20 mL) of 1-phenyl-3-hexanone and ethyl chloroacetate was added at 30° C.-40° C. over 2 hr in a thin stream. The mixture was stirred at 30° C. for 1 hr, and 10% hydrochloric acid (30 mL) was added for partitioning, which have a THF solution containing ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate (10.2 g, 76%; quantified by absolute calibration curve method (external standard method) using HPLC).

Workup

stirringThe mixture was stirred at 30° C. for 1 hr
customfor partitioning
additioncontaining ethyl 3-hydroxy-3-(2-phenylethyl)hexanoate (10.2 g, 76%; quantified by absolute calibration curve method (external standard method) using HPLC)

Sources & evidence

ORD record: ord-928049d8df4441eb8efe703a9b508b69
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07038075B2

Reaction notes

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