Tetralin → 6,10,14-Trimethyl-5-pentadecen-2-one

HRID 1283515Notes

Reaction equation

C1C2C(=CC=CC=2)CCC1.[CH3:11][C:12](O)([CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH:13]=[CH2:14].[CH2:27]=[C:28]1[O:32]C(=O)[CH2:29]1>>[CH3:11][C:12]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:13][CH2:14][CH2:27][C:28](=[O:32])[CH3:29]

Participants

Reactant 3

HCID 8404Tetralin

HCID 12661Diketene

HCID 5288243,7,11-Trimethyldodec-1-en-3-ol

Product 1

HCID 534359106,10,14-Trimethyl-5-pentadecen-2-oneYield 84.7%

Procedure

The procedure was the same as in Example 2 except that the diluent solvent was 10 g of tetraline and the starting reactants were 226 g (1.0 mole) of 3,7,11-trimethyl-1-dodecen-3-ol and 101 g (1.2 moles) of diketene. 6,10,14-Trimethyl-5-pentadecen-2-one with the boiling point of 123° to 125°C/1 mmHg and the refractive index of 1.4560 at 20°C was obtained in an amount of 212 g corresponding to 84.7% yield based on 3,7,11-trimethyl-1-dodecen-3-ol.

Sources & evidence

ORD record: ord-b381064561ba48638db806fd7b191659
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03975446

Reaction notes

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