Ethyl Bromide → 7-Hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne

HRID 2397667Notes

Reaction equation

HRID 2397667 reaction equation
C(Br)C.[Mg].[OH:5][C:6]([CH3:16])([CH:9]=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=[CH2:14])[C:7]#[CH:8].[CH3:17][C:18]1([CH3:26])[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[C:19]1=[O:25].[Cl-].[NH4+]>C(OCC)C.C1C=CC=CC=1>[OH:5][C:6]([CH3:16])([C:7]#[C:8][C:19]1([OH:25])[CH:20]([CH3:24])[CH2:21][CH2:22][CH2:23][C:18]1([CH3:26])[CH3:17])[CH:9]=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=[CH2:14]

Participants

8

Reactant 5

HCID 6332Ethyl BromideHCID 170002,2,6-TrimethylcyclohexanoneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 542483613,7-Dimethylnona-4,6,8-trien-1-yn-3-ol

Product 1

HCID 543180627-Hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl bromide (1.75 g.) in diethyl ether was added to a suspension of magnesium (0.385 g.) in ether and the mixture was heated to reflux for 30 minutes. A solution of the alcohol, 3-hydroxy-3,7-dimethyl-nona-4,6,8-trien-1-yne, (1.0 g.) in dry benzene was added and the mixture refluxed 30 minutes. A solution of 2,2,6-trimethylcyclohexanone (1.12 g.) in benzene was added and the mixture refluxed for 15 minutes and poured into saturated aqueous ammonium chloride solution. The organic phase was washed with brine dried and concentrated to give 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcyclohexyl)-nona-1,3,5-trien-8-yne which was chromatographed on activity III alumina to give pure 7-hydroxy-3,7-dimethyl-9-(1-hydroxy-2,2,6-trimethylcycohexyl)-nona-1,3,5-trien-8-yne.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture refluxed 30 minutes
  4. temperaturethe mixture refluxed for 15 minutes
  5. washThe organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40ac123dd7b44d859b026c45faa4490a
Source dataset
uspto-grants-1977_05
Patent number
US04022807

Reaction notes

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