1-Phenylethanol → 1,1',1''-(1-Methyl-1,3,5-pentanetriyl)tris(benzene)

HRID 256485

Reaction equation

HRID 256485 reaction equation
C(C1C=CC=CC=1)(CC)C.[Na].[CH3:12][CH:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C=CC1C=CC=CC=1.[C:29]1([CH2:35][CH2:36][C:37]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)(C)[CH2:38]C)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO>[C:14]1([CH2:13][CH2:12][CH:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:36][CH:37]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH3:38])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 74091-PhenylethanolHCID 7501StyreneHCID 8680Sec-Butylbenzene2×HCID 3253992Benzene, 1,1'-(1-ethyl-1-methyl-1,3-propanediyl)bis-HCID 5360545Sodium2×

Product 1

HCID 865381,1',1''-(1-Methyl-1,3,5-pentanetriyl)tris(benzene)Yield 460%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

A one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit, a reflux condenser with a calcium chloride tube, and a thermometer was charged with 268 grams (2.0 moles) of purified secondary butylbenzene, 4.0 grams (0.17 mole) of metallic sodium and 2.4 grams (0.02 moles) of α-phenethyl alcohol while introducing argon gas through the gas introduction conduit, and the resulting mixture was heated to 135° C. Then 69 grams (0.66 mole) of purified styrene and 20 grams (0.15 mole) of secondary butylbenzene were dropped thereto over 2 hours while maintaining the temperature of the reaction system at 135° C. After dropwise addition was completed, the reaction mixture was stirred while heating for 1 hour and then cooled to room temperature. An excess of metallic sodium was decomposed by dropping methanol in small portions while stirring. Introduction of argon gas was stopped, and the contents were transferred to a separating funnel and then washed with water. The aqueous laer was removed, and the remaining oily layer was analyzed by gas chromatography. This gas chromatographic analysis showed that 40.7 grams (0.17 mole) of 1,3-dipenyl-3-methylpentane and 31.4 grams (0.092 mole) of 1,3,5-triphenyl-5-methylpentane were formed. The total yield (per styrene) was 54 mole %.

Workup

  1. customA one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit, a reflux condenser with a calcium chloride tube
  2. additionwhile introducing argon gas through the gas introduction conduit
  3. temperatureover 2 hours while maintaining the temperature of the reaction system at 135° C
  4. additionAfter dropwise addition
  5. temperaturewhile heating for 1 hour
  6. temperaturecooled to room temperature
  7. stirringwhile stirring
  8. customthe contents were transferred to a separating funnel
  9. washwashed with water
  10. customThe aqueous laer was removed

Sources & evidence

ORD record
ord-5e255eff820845aabc5c7bc4b2b207b6
Source dataset
uspto-grants-1987_10
Patent number
US04703124

Linked notes

Loading…