Methanol → 1-(3,3-Dimethyl-cyclohex-6-en-1-yl)-pent-4-en-1-yne

HRID 25886Notes

Reaction equation

HRID 25886 reaction equation
CO.[CH3:3][C:4]1([CH3:15])[CH2:9][CH2:8][CH2:7][C:6]([C:10]#[C:11][CH2:12][CH:13]=[CH2:14])=[CH:5]1>O>[CH3:3][C:4]1([CH3:15])[CH2:9][CH2:8][CH:7]=[C:6]([C:10]#[C:11][CH2:12][CH:13]=[CH2:14])[CH2:5]1

Participants

4

Reactant 2

HCID 887MethanolHCID 205694151-(3,3-Dimethyl-cyclohex-1-en-1-yl)-pent-4-en-1-yne

Product 1

HCID 205694341-(3,3-Dimethyl-cyclohex-6-en-1-yl)-pent-4-en-1-yneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(c') 7 g of the above prepared carbinol were heated in a distillation apparatus in the presence of 2 g of H3BO3 at 12 Torr until no further formation of water was observed. The temperature was then slowly increased to 120°-130° and a 2:3 mixture of 1-(3,3-dimethyl-cyclohex-1-en-1-yl)-pent-4-en-1-yne and 1-(3,3-dimethyl-cyclohex-6-en-1-yl)-pent-4-en-1-yne was obtained (5.3 g; 70% yield). The subsequent conversion to the desired cyclohexenic ketones is effected according to the procedure given above (pathway I) paragraph d)

Workup

  1. temperatureThe temperature was then slowly increased to 120°-130°

Sources & evidence

ORD record
ord-f2584aedc74644f88f95e5830755c5cc
Source dataset
uspto-grants-1979_04
Patent number
US04147672

Reaction notes

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