tert-Butyl 4-(4-hydroxybut-1-yn-1-yl)benzoate → Benzoic acid, 4-(4-hydroxybutyl)-, 1,1-dimethylethyl ester

HRID 1675668Notes

Reaction equation

HRID 1675668 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:8][CH:7]=1>C(O)C.C(OCC)(=O)C.[Pt](=O)=O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 58024754tert-Butyl 4-(4-hydroxybut-1-yn-1-yl)benzoate2×

Product 1

HCID 10422229Benzoic acid, 4-(4-hydroxybutyl)-, 1,1-dimethylethyl esterYield 92.9%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,1-dimethylethyl 4-(4-hydroxy-1-butyn-1-yl)benzoate (0.9 g, e.g. which can be as prepared in Intermediate 22) in a mixture of ethanol (50 ml) and ethyl acetate (5 ml) was hydrogenated over platinum(IV) oxide (PtO2, 0.09 g, 10% w/w) for 18 hours at room temperature. The mixture was filtered through a bed of Celite, washing through with ethanol. The solvents were evaporated to dryness to give the title compound as a yellowy/brown oil (0.85 g). 1H NMR (400 MHz, chloroform-d) δ (delta) ppm 1.60 (14H, m), 1.70 (2H, m), 2.70 (2H, t, J=7.53 Hz & 7.78 Hz), 3.67 (2H, t, J=6.53 Hz & 6.27 Hz) 7.23 (2H, d, J=8.28 Hz), 7.91 (2H, d, J=8.03 Hz). Extra protons at about 1.5-1.6 ppm may perhaps be due to residual H2O in CDCl3. LCMS showed TRET=3.26 min with: MH+ not seen, and [MH]++18 adduct=268.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. washwashing through with ethanol
  3. customThe solvents were evaporated to dryness

Sources & evidence

ORD record
ord-db7d539c4c0a4b06848b4e6ae0b4a6b4
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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