Hydrochloric Acid → HCID 20165401, compound

HRID 255973Notes

Reaction equation

HRID 255973 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 3N hydrochloric acid while stirring, causing product to precipitate. It was collected by filtration, washed once with 25 parts 2N 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 2N 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-b04457f725e144b7930efe55def56712
Source dataset
uspto-grants-1987_10
Patent number
US04699997

Reaction notes

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