Benzoic Acid → Isodecanol

HRID 2254699Notes

Reaction equation

HRID 2254699 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1(C)[CH:15]=CC=C[CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O-]Cl.[Na+]>O>[CH2:1]([OH:9])[CH2:2][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:10]([CH3:15])[CH3:11]

Participants

6

Conditions

Temperature
100 °C

Procedure

2 moles); benzoic acid (250 grams; 2.05 moles), toluene (100 ml) and para toluene sulfonic acid (2 grams) were placed into a glass reaction flask equipped with stirrer, thermometer, heating mantle, 12" column packed with 1/4" glass rings, Dean-Stark water trap, and condenser. The temperature increased from 26° C. to 187° C. as the reaction proceeded with stirring Then the reaction mixture was cooled to 100° C. Soda ash (100 ml; 20% solution) was added to the mixture and was followed by the addition of a mixture of soda ash (50 ml; 20% solution) and chlorox (100 ml) at 81°-100° C. The alkaline bottom layer was separated from the mixture. After the mixture was dried, the toluene was removed by heating the mixture to 178° C. at 45 mmHg. The desired product (515 grams) was obtained after filtration, representing a yield of 98.3%.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer, heating mantle, 12" column
  3. temperatureThe temperature increased from 26° C. to 187° C. as the reaction
  4. customThe alkaline bottom layer was separated from the mixture
  5. customAfter the mixture was dried
  6. customthe toluene was removed
  7. temperatureby heating the mixture to 178° C. at 45 mmHg

Sources & evidence

ORD record
ord-944a82c55fe048f88448e37631f7a6f4
Source dataset
uspto-grants-1993_08
Patent number
US05236987

Reaction notes

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