Dichloroacetic Acid → (+)-alpha-Terpineol

HRID 1285629Notes

Reaction equation

HRID 1285629 reaction equation
ClC(Cl)C(O)=[O:4].[CH3:7][C:8]1[C@@H:13]2[C:14]([CH3:16])([CH3:15])[C@@H:11]([CH2:12]2)[CH2:10][CH:9]=1>O>[CH3:7][C:8]1[CH2:13][CH2:12][C@@H:11]([C:14]([OH:4])([CH3:16])[CH3:15])[CH2:10][CH:9]=1

Participants

4

Reactant 2

HCID 6597Dichloroacetic AcidHCID 82227alpha-Pinene, (+)-

Product 1

HCID 442501(+)-alpha-TerpineolYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following a procedure described in Matsubara, et al., Chem. Abstr., 84:165069b (1976), 64.5 g of dichloroacetic acid was added dropwise over 20 minutes at 5°-6° C. to a magnetically stirred mixture of 68.0 g of (+)-alpha-pinene ([alpha]D +47.1°) and 9.0 g of water. After stirring overnight at 5°-30° C. (ice allowed to melt slowly), the mixture was extracted with 400 ml of methylene chloride. The extract was washed successively with water, aqueous potassium carbonate solution and water, dried and Claisen distilled at 4 mm to give 11.2 g of forecut, b.p. 40°-71° C. and 47.5 g of the desired (+)-alpha-terpineol, b.p. 71°-83° C. Redistillation through a micro Vigreaux column gave 40.5 g of (+)-alpha-terpineol with [alpha]D +79.3° (CHCl3), b.p. 58°-60° C. (1 mm).

Workup

  1. extractionwas extracted with 400 ml of methylene chloride
  2. washThe extract was washed successively with water, aqueous potassium carbonate solution and water
  3. customdried
  4. distillationClaisen distilled at 4 mm

Sources & evidence

ORD record
ord-04ec761001d54e468a5bf7e2660d23a2
Source dataset
uspto-grants-1986_01
Patent number
US04567283

Reaction notes

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