Acrolein → HCID 21249528, compound

HRID 1531599Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]([CH3:8])[CH2:5][CH2:6]Br.[CH:9]([CH:11]=[CH2:12])=[O:10]>>[CH3:8][CH:4]([CH2:5][CH2:6][CH:9]([OH:10])[CH:11]=[CH2:12])[CH2:3][CH2:2][CH:9]([OH:10])[CH:11]=[CH2:12]

Participants

Reactant 2

HCID 7847Acrolein

HCID 1382581,5-Dibromo-3-methylpentane

Product 1

HCID 21249528HCID 21249528, compoundYield 78%

Procedure

Preparation ofthe di-Grignard reagent from 1,5-dibromo-3-methylpentane (46 g, 189 mmole) and treatment with acrolein (23.3 g, 415 mmole), as described in Example 6 (Step 2/Method A), gave 6-methylundeca-1,10-diene-3,9-diol (29.2 g, 78% yield). C12H22O2 (198.31 g/mole). bp: 115° C., 0.4 mm Hg. 1HNMR (500 MHz, CDCl3): 0.86 (d, 3H), 1.08-1.58 (m, 9H), 1.95 (bs, 2H), 4.02 (m, 2H), 5.06 (d, 2H), 5.18 (m, 2H), 5.79-5.87 (m, 2H) ppm. 13CNMR (125 MHz, CDCl3): 19.66, 32.38, 32.66, 32.77, 34.47, 73.50, 73.67, 114.62, 114.70, 141.32, 141.38. IR (νmax(cm−1)): 3360(bs), 3080(w), 2925(s), 2860(s), 1645(w), 1430(w), 995(s), 920(s). MS (m/z): 165(M-33), 151, 147, 109, 95, 81, 67, 57, 41.

Sources & evidence

ORD record: ord-587b18721387495380f4ace8091d2b75
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200254B1

Reaction notes

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