Water → HCID 13878907, compound

HRID 579913Notes

Reaction equation

HRID 579913 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].B.[Na].O>C(O)(C)C>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 13878906HCID 13878906, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 13878907HCID 13878907, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
70 °C

Procedure

4'-Octyloxy-4-formyl-biphenyl (30 g) was suspended in isopropyl alcohol (100 ml), followed by pouring in the resulting suspension, a suspension of sodium boron hydride (1.22 g) in isopropyl alcohol (100 ml), stirring the mixture at 70° C. for 4 hours, adding 6H-HCl (20 ml) and water (10 ml), stirring the mixture at 70° C. for 2 hours, allowing to stand overnight, filtering and collecting the resulting crystals and recrystallizing from ethanol to obtain 4'-octyloxy-4-hydroxymethyl-biphenyl (28.5 g) having a m.p. of 141.6° C. This product (16 g) together with thionyl chloride (12 g) were heated for 6 hours, followed by distilling off excess thionyl chloride and recrystallizing the residue from toluene-heptane to obtain 4'-octyloxy-4-chloromethyl-biphenyl (IIa-8) (14.8 g) having a m.p. of 101° C.

Workup

  1. additionby pouring in the resulting suspension
  2. stirringstirring the mixture at 70° C. for 2 hours
  3. waitto stand overnight
  4. filtrationfiltering
  5. customcollecting the resulting crystals
  6. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-c3c25d905c2241c38bc83679b1cc4438
Source dataset
uspto-grants-1988_06
Patent number
US04751019

Reaction notes

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