1,2-Dichloroethane → HCID 135702324, compound

HRID 1703567Notes

Reaction equation

HRID 1703567 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[S:7])=[CH:4][CH:3]=1.C(Cl)CCl.[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:20]=1[OH:29])([CH3:18])([CH3:17])[CH3:16].Cl>[Ti](Cl)(Cl)(Cl)Cl.CCCCCC>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:23]2[CH:22]=[C:21]([C:25]([CH3:26])([CH3:27])[CH3:28])[C:20]([OH:29])=[C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:24]=2)=[S:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 111,2-Dichloroethane2×HCID 313Hydrochloric AcidHCID 314052,6-Di-tert-butylphenolHCID 155550054-Methylthiobenzoyl chloride

Product 1

HCID 135702324HCID 135702324, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8058HexaneSolvent

Procedure

A solution of 54.5 g. (0.29 mole) of 4-methylthiobenzoyl chloride in 200 ml. of dichloroethylene is added gradually to 55 g. (0.29 mole) of titanium tetrachloride. After cooling this mixture, a solution of 60 g. of 2,6-di(t-butyl)phenol in 200 ml. of dichloroethylene is added. The resulting mixture is stirred for several hours, then hydrolyzed with 10 percent hydrochloric acid. The organic layer is separated, washed with water, dried and evaporated to provide a yellow oil. This product is mixed with hexane to provide a white solid which is recrystallized from hexane to provide 4-(4-methylthiobenzoyl)-2,6-di(t-butyl)-phenol, m.p. 135°-136° C.

Workup

  1. temperatureAfter cooling this mixture
  2. customThe organic layer is separated
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customto provide a yellow oil
  7. customto provide a white solid which
  8. customis recrystallized from hexane

Sources & evidence

ORD record
ord-e92c6414965f4fe6aefa40333dbff8e7
Source dataset
uspto-grants-1978_11
Patent number
US04124725

Reaction notes

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