Hydrochloric Acid → HCID 73689151, compound

HRID 565160Notes

Reaction equation

HRID 565160 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19]C(C=O)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].O.Cl.[CH2:32]1[CH2:36]O[CH2:34][CH2:33]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH:32]([CH:36]1[CH2:19][CH2:20][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([C:8]#[C:7][C:4]3[CH:3]=[CH:2][C:1]([CH3:23])=[CH:6][CH:5]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1)=[CH:33][CH3:34]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 86756213HCID 86756213, compound

Product 1

HCID 73689151HCID 73689151, compound

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

14.03 g of 4-(4-p-tolylethynylphenyl)cyclohexanecarbaldehyde were dissolved in 100 ml of THF, and 15.22 g of ethyltriphenylphosphonium bromide were added quickly under a nitrogen atmosphere. 4.6 g of potassium tert-butoxide were then added in portions. The suspension was stirred overnight at RT, then poured into water and neutralized using 2 N hydrochloric acid solution. Conventional work-up gave 1-propenyl-4-(4-p-tolylethynylphenyl)cyclohexane as an E/Z isomer mixture.

Sources & evidence

ORD record
ord-2717ecce04344f8e8bbe43e1cba24dc5
Source dataset
uspto-grants-2001_01
Patent number
US06171664B2

Reaction notes

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