Ethyl Acetate → 2-Undecanone

HRID 2308400Notes

Reaction equation

HRID 2308400 reaction equation
C[C:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]CC)=[CH:3][CH2:4][OH:5].[C:15](OCC)(=O)C>[Pd]>[CH3:15][C:4](=[O:5])[CH2:3][CH2:2][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 85044737HCID 85044737, compound

Product 1

HCID 81632-Undecanone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Pd-C (1.0 g) was added to an ethyl acetate solution (300 ml) of 3-methyl-2-dodecen-1-ol (3″) (30 g, 0.15 mol) obtained from 2-undecanone (1″) in the same manner as in Example 2, and the mixture was stirred for 3 days in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate obtained was concentrated and then distilled under reduced pressure to obtain 3-methyldodecan-1-ol (4″) (20 g, 67%). b.p. 122-123° C./4 torrs. 1H-NMR (90 MHz, CDCl3) 0.8-1.0 (6H,m,Me), 1.0-1.7 (20H,m,2˜11-H and OH), 3.66 (2H,q,J=7,1-H).

Sources & evidence

ORD record
ord-bf4159a055174ad8b20dc656e864def3
Source dataset
uspto-grants-2004_12
Patent number
US06835846B2

Reaction notes

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