Hydrochloric Acid → HCID 15114149, compound

HRID 979420Notes

Reaction equation

HRID 979420 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH3:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C@@H:32](O)[CH3:33].[CH2:35]([O:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47]Br)=[CH:45][CH:44]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].Cl>C1COCC1.CS(C)=O>[CH2:35]([O:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH:32]([CH3:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH3:26])=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[CH:45][CH:44]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 71124,4'-DihydroxybiphenylHCID 85570p-ToluenesulfonateHCID 2723888(+)-2-OctanolHCID 156812701-(Bromomethyl)-4-(heptyloxy)benzene

Product 1

HCID 15114149HCID 15114149, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.8 g) was decanted twice with n-heptane (20 ml), successively with THF (20 ml) and placed in a flask in the form of a suspension in THF (20 ml), followed by dropwise adding a solution of 4'-hydroxy-4-(1-methylheptyloxy)-biphenyl (IIIa-7) of m.p. 98.1° C. (5.1 g) obtained by reacting 4,4'-dihydroxybiphenyl with a tosylate derived from S-(+)-2-octanol, in THF (30 ml), thereafter dropwise adding DMSO (20 ml), successively dropwise adding a solution of p-heptyloxybenzyl bromide (5.4 g) in DMSO (30 ml), stirring the mixture at room temperature, allowing to stand overnight, adding 6N-HCl (200 ml), extracting with toluene, washing with acid, washing with alkali, washing with water to make it neutral, drying, concentrating, subjecting the concentrate to column chromatography with activated alumina (20 g) to effect separation-concentration using toluene as an elute, and twice recrystallizing from a mixed solvent of ethanol (40 ml) and ethyl acetate (20 ml) to obtain the captioned 4'-(p-(heptyloxy)phenylmethyloxy)-4-(1-methylheptyloxy)biphenyl (3.6 g). Its m.p., etc. are described in Table 2. Further its elementary analysis values accorded well with its calculated values as follows:

Workup

  1. customSodium hydride (0.8 g) was decanted twice with n-heptane (20 ml), successively with THF (20 ml)
  2. customplaced in a flask in the form of a suspension in THF (20 ml)
  3. additionby dropwise adding a solution of 4'-hydroxy-4-(1-methylheptyloxy)-biphenyl (IIIa-7) of m.p. 98.1° C. (5.1 g)
  4. customobtained
  5. extractionextracting with toluene
  6. washwashing with acid
  7. washwashing with alkali,
  8. washwashing with water
  9. customdrying
  10. concentrationconcentrating
  11. concentrationconcentrate to column chromatography with activated alumina (20 g)
  12. concentrationseparation-concentration
  13. customtwice recrystallizing from a mixed solvent of ethanol (40 ml) and ethyl acetate (20 ml)

Sources & evidence

ORD record
ord-d06076c7d38e42939cdd17c233c49785
Source dataset
uspto-grants-1987_05
Patent number
US04668427

Reaction notes

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