Hydrochloric Acid → 1-Dodecanol

HRID 1583838Notes

Reaction equation

HRID 1583838 reaction equation
[Na].C(O)C.[N+]([CH:8]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:20])([O-])=O.Cl>C(Cl)Cl.O.C(O)C.O>[CH2:9]([OH:20])[CH2:8][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 3344472-NitrocyclododecanoneHCID 5360545Sodium

Product 1

HCID 81931-Dodecanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
15 °C

Procedure

For purposes of analytical determinations, the process of Example 2 was carried out with sodium boroduteride (NaBD4) To 40 milliliters of absolute ethanol was added about 2.5 grams of NaBD4 (0.05972 mole). The suspension was stirred and about 6.78 grams (0.02986 mole) solid 2-nitro cyclododecan-1-one were added in portions maintaining the temperature at about 15° C. The addition took about 20 minutes and some foaming was evidenced (gas evolution). After the addition was complete, a white, fairly thick precipitate was evident. An additional 10 milliliters of ethanol was added to facilitate stirring. The reaction mass was allowed to warm to room temperature and stirred overnight. The acidification process of the previous examples was followed and the precipitate again disappeared at a pH of 2 after addition of about 100 milliliters of 2% HCl. The solution had a fine white appearance. The ethanol/water was stripped to about 1/2 the starting volume and the water-oil emulsion left was taken up in methylene chloride. After two washings with methylene chloride, the combined organic layers were dried over magnesium sulfate and the solvent stripped off and vacuumed. A yellow oil was recovered which solidified fairly rapidly. The material melts at 40° C. and approximately 6.95 grams of product were recovered. Using the deuterium ions supplied in place of hydride ions from the NaBD4, the nuclear magnetic resonance spectroscopy confirmed the ring opening of the cyclic compound to form a dodecanol having a nitro substituent at the opposite end of the hydroxy function. Furthermore, the analysis confirmed that the carbonyl function had been converted to the hydroxy function.

Workup

  1. additionwas added about 2.5 grams of NaBD4 (0.05972 mole)
  2. additionThe addition
  3. additionAfter the addition
  4. stirringto facilitate stirring
  5. temperatureto warm to room temperature
  6. stirringstirred overnight
  7. washAfter two washings with methylene chloride
  8. dry with materialthe combined organic layers were dried over magnesium sulfate
  9. customA yellow oil was recovered which
  10. customThe material melts at 40° C. and approximately 6.95 grams of product were recovered

Sources & evidence

ORD record
ord-2b2461145c314bbaaafa3be5b5c295d1
Source dataset
uspto-grants-1985_11
Patent number
US04554387

Reaction notes

Loading…