Hydrochloric Acid → HCID 54085422, compound

HRID 1730739Notes

Reaction equation

HRID 1730739 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17](O)[CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.COC1C=CC(C2C=CC(C(Cl)C)=CC=2)=CC=1.Cl.[CH3:38][O:39][C:40](=[O:43])[CH2:41][SH:42].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C1CCCCC1.CO>[CH3:38][O:39][C:40](=[O:43])[CH2:41][S:42][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1)[CH3:18]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 4311764Sodium borohydrideHCID 14533349HCID 14533349, compoundHCID 203487384-(1-Chloroethyl)-4'-methoxy-1,1'-biphenyl2×

Product 1

HCID 54085422HCID 54085422, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8078CyclohexaneSolvent

Procedure

(4'-Methoxy-4-biphenyl)-methyl-ketone [see W. S. Johnson et al, J. Amer. Chem. Soc. 68, 1648 (1946)] was reduced with sodium borohydride to 1-(4'-methoxy-4-biphenylyl)-ethanol (m.p. 120°-122° C, from cyclohexane), and the carbinol was converted into 1-(4'-methoxy-4-biphenylyl)-1-chloroethane, m.p. 122°-124° C (from cyclohexane), with hydrogen chloride. 5.2 gm of 1-(4'-methoxy-4-biphenylyl)-1-chloroethane (0.021 mol) were admixed in 21 ml of dry dimethyl sulfoxide with 2.7 gm (0.026 mol) of thioglycolic acid methyl ester and then with 3.5 gm (0.026 mol) of dry potassium carbonate. The mixture was stirred at room temperature for 45 minutes. The reaction product was precipitated with water, suction-filtered off, washed and dried. Yield: 6.8 gm (100% of theory); m.p. 59°-61° C. A sample recrystallized from cyclohexane, analized as follows:

Workup

  1. customThe reaction product was precipitated with water
  2. filtrationsuction-filtered off
  3. washwashed
  4. customdried
  5. customA sample recrystallized from cyclohexane

Sources & evidence

ORD record
ord-ce26b216ca0a45ef814b994e543386e9
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

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