Hydrochloric Acid → HCID 20165401, compound

HRID 1758282Notes

Reaction equation

HRID 1758282 reaction equation
CN(C)[CH2:3][CH2:4]N(C)C.[CH2:9]([OH:21])[CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:15]#[C:16][CH2:17][CH2:18][C:19]#[CH:20].Cl.[CH:23]([OH:30])(O)[C:24]#[C:25][CH2:26][CH2:27][CH3:28]>CO.O=O>[CH2:23]([OH:30])[CH2:24][CH2:25][CH2:26][C:27]#[C:28][C:9]#[C:10][CH2:11][CH2:12][C:3]#[C:4][C:20]#[C:19][CH2:18][CH2:17][C:16]#[C:15][C:14]#[C:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 934535,7,11-Dodecatriyn-1-olHCID 71355601Hex-2-yne-1,1-diol

Product 1

HCID 20165401HCID 20165401, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 977OxygenSolvent

Procedure

A mixture of 2 parts cuprous chloride, 12 parts methanol, and 4 parts N,N,N',N'-tetramethylethylenediamine was prepared. To this mixture over a period of 15 minutes was added 5,7,11-dodecatriyn-1-ol (produced in Part A above) dissolved in 12 parts methanol, while oxygen was moderately bubbled through the reaction contents. After 1 hour, oxygen flow was stopped and the methanol was distilled leaving a semi-viscous residue. To this was added 100 parts of 3 N hydrochloric acid while stirring, causing product to precipitate. It was collected by filtration, washed once with 25 parts 2 N hydrochloric acid and several times with water. The solid was dissolved in 200 parts xylene and the solution was refrigerated at -8° C. Subsequent crystallization and filtration yielded 6.0 parts of fluffy product, the above hexayne diol, which turns blue in daylight. The melting point of the material was 101.0° to 104.1° C.

Workup

  1. customwas prepared
  2. customproduced in Part A above)
  3. customwas moderately bubbled through the reaction contents
  4. distillationthe methanol was distilled
  5. customleaving a semi-viscous residue
  6. customto precipitate
  7. filtrationIt was collected by filtration
  8. washwashed once with 25 parts 2 N hydrochloric acid and several times with water
  9. dissolutionThe solid was dissolved in 200 parts xylene
  10. customwas refrigerated at -8° C
  11. customSubsequent crystallization and filtration
  12. customyielded 6.0 parts of fluffy product
  13. customwas 101.0° to 104.1° C.

Sources & evidence

ORD record
ord-eb75ae1d364244938e0be62bc8779730
Source dataset
uspto-grants-1983_02
Patent number
US04373032

Reaction notes

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