Acetic Acid → Decane

HRID 1834510Notes

Reaction equation

HRID 1834510 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7](CC(C)C)[CH:6]=[C:5](C(F)(F)F)[C:4]=1[OH:17].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(O)(=O)C>C1C=CC=CC=1>[O:17]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:2]=[N:1][CH2:18]1.[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 15600DecaneHCID 20326862HCID 20326862, compound

Product 2

HCID 15600DecaneHCID 2762566HCID 2762566, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-aminomethyl-4-(2,2-dimethylethyl)-6-trifluoromethylphenol (1.24 g., 0.005 mole), 2-oxotricyclo(3.3.1.1.3,7)decane (0.75 g., 0.005 mole) and acetic acid (0.25 ml.) in dry benzene (50 ml.) is refluxed under a constant water separator for 3 hr. The solution is cooled, washed with 2% sodium hydroxide solution, water and salt brine and then dried (MgSO4) and evaporated under reduced pressure. The solid residue (1.2 g.) is crystallized from hexane to obtain 3,4-dihydro-6-(1,1-dimethylethyl)-8-trifluoromethylspiro[2H-1,3-benzoxazine-2,2'-tricyclo(3.3.1.1.3,7)decane] (0.65 g.), m.p. 125°-126.5° C.

Workup

  1. temperatureThe solution is cooled
  2. washwashed with 2% sodium hydroxide solution, water and salt brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe solid residue (1.2 g.) is crystallized from hexane

Sources & evidence

ORD record
ord-fe08c85d261c4114bdce46c26ccc8eed
Source dataset
uspto-grants-1978_01
Patent number
US04070464

Reaction notes

Loading…