Hydrochloric Acid → Methyl 3-hydroxy-3-isopropyl-7-phenylheptanoic acid

HRID 1107145Notes

Reaction equation

[OH:1][C:2]([CH:18]([CH3:20])[CH3:19])([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]([O:6]C)=[O:5].[CH3:21]O.Cl>O>[CH3:21][CH:3]([C:2]([OH:1])([CH:18]([CH3:20])[CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 0.88 g (3.17 mmol) of the methyl 3-hydroxy-3-isopropyl-7-phenylheptanoate in 30 mL of 1:1:1-THF:MeOH:H2O is added 1.08 g (25.36 mmol, 8 eq) of LiOH monohydrate and this is stirred at 25° C. for 1 month. This mixture is then acidified to pH=6 with 1 N HCl and then partitioned between ethyl acetate and water. The organics are dried (Na2SO4) and concentrated in vacuo to afford methyl 3-hydroxy-3-isopropyl-7-phenylheptanoic acid in the form of a pale yellow crystalline solid. (0.59 g, 70%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 0.98(d, 6H), 1.35(m, 1H), 1.55(m, 5H), 2.1(m, 1H), 2.35(t, 1H), 2.6(t, 2H), 3.88(m, 1H), 6.08(bs, 2H), 7.15(m, 3H), 7.25(m, 2H).

Workup

custompartitioned between ethyl acetate and water
dry with materialThe organics are dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f6c69e02109e49e3ae604755daf56afa
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057369

Reaction notes

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