Lithium Hydroxide → 4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid

HRID 736520Notes

Reaction equation

C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:28][CH3:29])([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([CH2:25][CH3:26])([OH:24])[CH2:22][CH3:23])=[C:15]([CH3:27])[CH:14]=2)[CH2:11][CH3:12])=[CH:6][C:5]=1[CH3:30].[OH-].[Li+]>>[CH2:11]([C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[C:5]([CH3:30])[CH:6]=1)([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([CH2:22][CH3:23])([OH:24])[CH2:25][CH3:26])=[C:15]([CH3:27])[CH:14]=1)[CH2:28][CH3:29])[CH3:12]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 57849336HCID 57849336, compound

Product 1

HCID 578493484-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acidYield 83.2%

Procedure

4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid methyl ester (2.20 g, 5.23 mmol) and lithium hydroxide (376 mg, 15.69 mmol) are reacted and purified analogous to Example 1I to give the title compound (1.77 g, 83%).

Workup

custompurified analogous to Example 1I

Sources & evidence

ORD record: ord-15f690a3d907415a970c881f6f321b8d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595345B2

Reaction notes

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