Lithium Hydroxide → 4-(5-Hydroxypent-1-yn-1-yl)benzoic acid

HRID 385257Notes

Reaction equation

[Li+].[OH-].[OH:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1.CCOC(C)=O>O.C1COCC1>[OH:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 42 °C

Procedure

LiOH (2 g, 83 mmol) in H2O (30 mL) was added dropwise to a stirring solution of Intermediate 20 (2 g, 9.2 mmol) in THF (30 mL). The resulting mixture was stirred at 42° C. for 4 h. After cooling, water (100 mL) and EtOAc (200 mL) were added. The mixture was extracted with EtOAc. The organic layer and the H2O layer were independently neutralized with 1N HCl. The aqueous layer was extracted with EtOAc and the combined organic layers dried over MgSO4 (s). The material was concentrated by rotary evaporation and the crude solid was purified by trituration with EtOAc and hexanes to give the title compound as a white powder (1.75 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 13.05 (brs, 1H), 7.88 (dd, 2H, J=8.5, 1.5 Hz), 7.47 (dd, 2H, J=8.5, 1.5 Hz), 4.55 (brs, 1H), 3.50 (t, 2H, J=5.5 Hz), 2.50 (m, 2H), 1.68 (m, 2H); ES/MS calcd. for C12H1O3+205.1. found m/z=205 (M+H)+.

Workup

temperatureAfter cooling
extractionThe mixture was extracted with EtOAc
extractionThe aqueous layer was extracted with EtOAc
dry with materialthe combined organic layers dried over MgSO4 (s)
concentrationThe material was concentrated by rotary evaporation
customthe crude solid was purified by trituration with EtOAc and hexanes

Sources & evidence

ORD record: ord-8d61b7b3ff3e4918a2a5475a59b5d88e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367829B2

Reaction notes

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