Chloroform → HCID 57085590, compound

HRID 570029Notes

Reaction equation

HRID 570029 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[C:23](CO)[CH:22]=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][C:12]=1[O:19][CH3:20].O=S(Cl)[Cl:29].CCCCCCC.[CH:38]([Cl:41])(Cl)Cl>>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([CH2:38][Cl:41])[CH:22]=[CH:21][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][Cl:29])=[CH:13][C:12]=1[O:19][CH3:20]

Participants

5

Reactant 4

HCID 6212Chloroform3×HCID 8900Heptane2×HCID 24386Thionyl ChlorideHCID 14140465{Butane-1,4-diylbis[oxy(3-methoxy-4,1-phenylene)]}dimethanol

Product 1

HCID 57085590HCID 57085590, compound

Procedure

A solution of 22 g 1,4-bis(2-methoxy-4-hydroxymethylphenoxy) butane in 200 ml warm CHCl3 was added dropwise to a solution of 60 ml SOCl2 in 100 ml CHCl3. After the addition was completed, the chloroform was boiled off while replacing with heptane. When the temperature reached the boiling point of heptane (97° C.), the solution was decanted from a small amount of yellow oil and allowed to cool. Decantation from oily impurities was continued until the white crystalline product began to form. The solution was cooled, and, after crystallization was completed, the product was filtered, washed with hexane, and air dried. One more recrystallization from heptane gave a pure-white crystalline product which was one spot on TLC. The yield was 23 grams, m.p. 116°-118° C.

Workup

  1. additionAfter the addition
  2. customthe solution was decanted from a small amount of yellow oil
  3. temperatureto cool
  4. customto form
  5. temperatureThe solution was cooled
  6. customafter crystallization
  7. filtrationthe product was filtered
  8. washwashed with hexane, and air
  9. customdried
  10. customOne more recrystallization from heptane
  11. customgave a pure-white crystalline product which

Sources & evidence

ORD record
ord-f6ed1ad88a84465e948415a6720cb5fc
Source dataset
uspto-grants-1988_03
Patent number
US04734458

Reaction notes

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