Hydrochloric Acid → HCID 21284620, compound

HRID 2231804Notes

Reaction equation

HRID 2231804 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[CH2:6]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2C(C(OC)=O)=CC=[CH:25][CH:26]=2)=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:6]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:3]=[CH:2][C:1]([CH2:5][OH:4])=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 21284618HCID 21284618, compound

Product 1

HCID 21284620HCID 21284620, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

200 ml of a THF solution of 32 g of methyl 4'-nonylbiphenylcarboxylate was slowly dropped to 300 ml of a THF solution of 3.5 g of lithium aluminum hydride while cooling with ice. After the completion of dropwise addition, the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was again cooled with ice, and 20 ml of ethyl acetate was slowly dropped thereto. Subsequently, 50 ml of water and 100 ml of 6 N hydrochloric acid were slowly dropped thereto. 300 ml of toluene was added thereto. An organic layer was washed with saturated saline water, with 6 N hydrochloric acid, with saturated saline water, with a 2 N sodium hydroxide aqueous solution and further with saturated saline water to make it neutral. The organic layer was dried over anhydrous magnesium sulfate, concentrated and then recrystallized from 200 ml of ethanol to obtain 28 g of 4'-nonyl-4-hydroxymethyl-biphenyl having a melting point of 101 to 102° C. Analysis of the above compound by HPLC showed that the purity was 99.9%. The total of the compound and 30 g of thionyl chloride were mixed and allowed to stand overnight. Then, the mixture was heated for 30 minutes on a water bath maintained at 70° C. and then allowed to cool. The mixture was poured into ice water and extracted with 300 ml of toluene. The extract thus obtained was washed with saturated saline water, with a saturated sodium hydrogencarbonate aqueous solution and further with saturated saline water, made neutral, dried over anhydrous magnesium sulfate, concentrated, and recrystallized from 300 ml of ethanol to obtain 25 g of 4'-nonyl-4-chloromethyl-biphenyl, having a melting point of 68.0 to 68.4° C. Analysis of the compound by HPLC showed that the purity was 99.8%.

Workup

  1. temperaturewhile cooling with ice
  2. additionAfter the completion of dropwise addition
  3. additionwas slowly dropped
  4. washAn organic layer was washed with saturated saline water, with 6 N hydrochloric acid, with saturated saline water, with a 2 N sodium hydroxide aqueous solution and further with saturated saline water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customrecrystallized from 200 ml of ethanol

Sources & evidence

ORD record
ord-8627eb245df14df7be95adfc631ab2aa
Source dataset
uspto-grants-1988_11
Patent number
US04784791

Reaction notes

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