1-Bromooctadecane → HCID 86735734, compound

HRID 838831Notes

Reaction equation

HRID 838831 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12]2([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=3)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[CH2:36](Br)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]>C(O)C>[CH2:53]([O:21][C:20](=[O:22])[CH2:19][CH2:18][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1([C:7]1[CH:8]=[CH:9][C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)[C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH3:36]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 14797Potassium HydroxideHCID 20324861HCID 20324861, compound

Product 1

HCID 86735734HCID 86735734, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

45.2 g (0.1 mol) of 2,2-bis-(3'-tert.butyl-4'-hydroxyphenyl)-cyclohexanepropionic acid are dissolved in ethanol and neutralizaed with an ethanolic solution of 5.7 g (0.1 mol) of potassium hydroxide. The solution is concentrated nearly to dryness, taken up in 250 ml of toluene and mixed with 33.3 g (0.1 mol) of octadecyl bromide. The batch is refluxed for 3 hours, filtered off from the precipitated KBr and concentrated to about 100 ml. The product precipitated after some time is recrystallized from toluene/heptane. Yield 50 g, which corresponds to 71 % of the theory. Melting point 155° C.

Workup

  1. concentrationThe solution is concentrated nearly to dryness
  2. temperatureThe batch is refluxed for 3 hours
  3. filtrationfiltered off from the precipitated KBr
  4. concentrationconcentrated to about 100 ml
  5. customThe product precipitated after some time
  6. customis recrystallized from toluene/heptane

Sources & evidence

ORD record
ord-9f1cb9570a7b43a0b7e53b415b55be59
Source dataset
uspto-grants-1978_06
Patent number
US04093592

Reaction notes

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