Dichloroacetic Acid → (+)-alpha-Terpineol

HRID 1248523Notes

Reaction equation

HRID 1248523 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-5702ef70021d479eafb00d5097a0ff16
Source dataset
uspto-grants-1985_06
Patent number
US04525203

Reaction notes

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