2,2-Dimethyl-4-[(1-oxodecyl)oxy]butanoic acid phenylmethyl ester → 2,2-Dimethyl-4-[(1-oxodecyl)oxy]butanoic acid

HRID 569506Notes

Reaction equation

HRID 569506 reaction equation
C1(C[O:8][C:9](=[O:27])[C:10]([CH3:26])([CH3:25])[CH2:11][CH2:12][O:13][C:14](=[O:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[CH3:26][C:10]([CH3:25])([CH2:11][CH2:12][O:13][C:14](=[O:24])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:9]([OH:27])=[O:8]

Participants

4

Reactant 1

HCID 141523052,2-Dimethyl-4-[(1-oxodecyl)oxy]butanoic acid phenylmethyl ester

Product 1

HCID 141523122,2-Dimethyl-4-[(1-oxodecyl)oxy]butanoic acidYield 96.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,2-dimethyl-4-[(1-oxodecyl)oxy]butanoic acid phenylmethyl ester (33.9 g), 20% Pd(OH)2 /C (2.0 g), and ethanol (150 mL) was hydrogenated at 50 psi at room temperature for 2 hours, filtered to remove the catalyst, and concentrated to afford 24.9 g (96.5%) of 2,2-dimethyl-4-[(1-oxodecyl)oxy]butanoic acid as a colorless oil. A portion was evaporatively distilled to afford an analytical sample: bp 190° C./0.02 mm; IR (CHC3) 1733 (C=O) and 1704 cm-1 (C=O); NMR (CDCl3) δ 0.87 (t, 3, CH3), 1.60-1.24 (m, 20, CH2 and CH3), 1.93 (t, 2, CH2), 2.25 (t, 2, CH2), 4.14 (t, 2, CH2); MS m/e 268 (M+ --H2O).

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-882ff32c5dd14c508a0b32d22738f559
Source dataset
uspto-grants-1988_03
Patent number
US04732902

Reaction notes

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